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

1211443-58-1 Synthesis

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

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

506-59-2 Synthesis

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

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

1211443-61-6
186 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
128 suppliers
$23.00/100mg