ChemicalBook CAS DataBase List 2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide synthesis

7synthesis methods

Product Name: 2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide
CAS Number:1211443-61-6
Molecular formula:C14H17ClN4O
Molecular Weight:292.76

2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyriMidine-6-carboxylic acid

1211443-58-1

124-40-3

2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

1211443-61-6

To a three-necked flask was added 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-D]pyrimidine-6-carboxylic acid (26.57 g, 100 mmol) and N,N-dimethylformamide (133 mL), and the mixture was cooled to 0-5 °C under stirring. EDCI (23.00 g, 120 mmol) and a tetrahydrofuran solution of dimethylamine (2.0 M, 75 mL, 150 mmol) were then added. Triethylamine (20.24 g, 200 mmol) was added dropwise and the mixture was stirred at 20-25 °C for 6-8 hours. After completion of the reaction, the reaction mixture was extracted three times with ethyl acetate (133 mL) and the organic phases were combined. The organic phase was sequentially washed twice with water and once with brine (133 mL), dried with anhydrous sodium sulfate and concentrated. Finally, the target product 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (26.93 g, 92% yield) was purified by column chromatography in a mixed solvent of dichloromethane and methanol.

1211443-58-1 Synthesis

1211443-58-1
133 suppliers
$23.00/100mg

506-59-2 Synthesis

506-59-2
568 suppliers
$5.00/5G

1211443-61-6
197 suppliers
$18.00/250mg

Yield:1211443-61-6 99%

Reaction Conditions:

Stage #1: 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidwith O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate;triethylamine in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: N,N-dimethylammonium chloride in N,N-dimethyl-formamide at 20;Reagent/catalyst;

Steps:

1.1 Step 1 : (6-Chloro-l-cyclopentyl-l,5,7-triaza-lH-inden-2-yl)(dimethylamino)formaldehyde:

A stirring solution of 6-chloro-l-cyclopentyl-l,5,7-triaza-lH-indene-2-carboxylic acid (199 mg, 0.75 mmol) and triethylamine (631 L, 4.5 mmol) in DMF (4 mL) was treated with HBTU (427 mg, 1.13 mmol) in one portion. The resulting mixture was stirred at room temperature for 30 minutes. Dimethylamine hydrochloride salt (122 mg, 1.50 mmol) was added in one portion and the resulting solution was stirred at room temperature overnight. Next morning, LCMS analysis indicated clean conversion to product (m/z = 293.4). The reaction mixture was diluted with EtOAc, transferred to a separatory funnel and washed with 0.1 N HC1 aqueous and brine. The organics were dried over anhydrous MgS0₄, filtered and concentrated to yield the crude product. This was purified on a S1O2 column using a hexanes/EtOAc gradient eluent. The fractions containing the product were concentrated to yield 215 mg (0.74 mmol, 99 %). LC/MS - HPLC (254 nm) - Rt 2.90 min. MS (ESI) m/z 293.4 [M+ + H+].

References:

WO2018/140730,2018,A1 Location in patent:Paragraph 0218

1211443-58-1 Synthesis

1211443-58-1
133 suppliers
$23.00/100mg

124-40-3
549 suppliers
$18.00/100ml

1211443-61-6
197 suppliers
$18.00/250mg

References