Sodium hydride → HCID 11281976, compound

HRID 1958423Notes

Reaction equation

HRID 1958423 reaction equation
Cl.[CH2:2]([N:9]1[CH2:12][CH:11]([OH:13])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]2[N:23]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)[N:24]=[CH:25][C:18]=12>CC(N(C)C)=O>[CH2:2]([N:9]1[CH2:12][CH:11]([O:13][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([C:26]4[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][CH:31]=4)[N:24]=[CH:25][C:18]=23)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 218974474-Chloro-1-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidineHCID 57496374223382-13-6

Product 1

HCID 11281976HCID 11281976, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-Benzyl-azetidin-3-ol hydrochloride salt (0.59 mmol, 117 mg) and sodium hydride were dissolved in dimethyl acetamide (2 mL) and stirred at room temperature for 30 minutes. 4-Chloro-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (0.49 mmol, 150 mg) was added slowly and the mixture was stirred at 70° C. for 20 minutes. The reaction mixture was quenched with water followed by an extraction with ethyl acetate. Removal of organic solvents in vacuo and purification by flash chromatography provided compound A23 as a white solid (88 mg, 41%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.90 (s, 1H); 8.53 (s, 1H); 8.30 (d, 2H); 8.16 (d, 2H); 7.43 (m, 5H); 6.19 (m, 1H); 4.59 (m, 2H); 4.42 (d, 1H); 4.00 (d, 1H); 3.65 (d, 1H); 3.35 (m, 1H); 3.30 (s, 3H).

Workup

  1. stirringthe mixture was stirred at 70° C. for 20 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionfollowed by an extraction with ethyl acetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by flash chromatography

Sources & evidence

ORD record
ord-b862d6c7ffb44dc49753169686dae16c
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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