Sodium hydride → HCID 58959492, compound

HRID 915857Notes

Reaction equation

HRID 915857 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:17]1[C:18]2[C:19](=[C:23]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)[N:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[N:25]=2)[N:20]=[CH:21][N:22]=1>CN(C)C=O.C(OC)(C)(C)C>[CH2:3]([N:10]1[CH2:14][CH2:13][CH:12]([O:15][C:17]2[C:18]3[C:19](=[C:23]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[N:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])[N:25]=3)[N:20]=[CH:21][N:22]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 69889N-benzyl-3-pyrrolidinolHCID 58959477HCID 58959477, compound

Product 1

HCID 58959492HCID 58959492, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Sodium hydride (24 mg of a 60% dispersion in mineral oil, 0.6 mmol) was added to a solution of 1-benzylpyrrolidin-3-ol (0.1 ml, 0.6 mmol) in dimethylformamide (1 ml), and the resultant mixture was stirred at room temperature for 5 min. Next, 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine 1-2A-1c (50 mg, 0.13 mmol) was added in one portion, and the mixture was stirred for 2 hours. The reaction mixture was diluted with methyl tert-butyl ether and washed with water (3×). The organic phase was dried over anhydrous magnesium sulfate and concentrated. Purification of the residue by flash column chromatography (50% ethyl acetate in hexanes) provided the title compound 7-(1-benzylpyrrolidin-3-yloxy)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine 7A-1 (21 mg): MS: 516.1 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 8.6 (s, 1H), 7.5 (m, 6H), 7.3 (m, 7H), 5.8 (m, 1H), 3.7 (s, 2H), 3.2 (m, 1H), 2.9 (m, 1H), 2.8 (m, 1H), 2.7 (m, 1H), 2.5 (m, 1H), 2.2 (m, 1H).

Workup

  1. washwashed with water (3×)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customPurification of the residue by flash column chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4857b269d60247a083e3bf9812bdf113
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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