Sodium hydride → HCID 12051249, compound

HRID 2212963Notes

Reaction equation

HRID 2212963 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([OH:10])=[CH:8][N:7]=[C:6]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:5]=1.[N:28]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[N:28]1([C:33]([O:10][C:9]2[C:4]([NH2:3])=[N:5][C:6]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[N:12]=3)=[N:7][CH:8]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 135476485HCID 135476485, compound

Product 1

HCID 12051249HCID 12051249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 mg (0.15 mmol) of sodium hydride were added to a suspension of 50.0 mg (0.15 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinol from example IV in 2 ml of THF at RT. After the mixture had been stirred at RT for 30 min, 21.8 mg (0.16 mmol) of 1-pyrrolidinecarbonyl chloride were added and the mixture was stirred at RT overnight. The product was purified by thin-layer chromatography (silica gel, CH2Cl2/MeOH 10:1).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe product was purified by thin-layer chromatography (silica gel, CH2Cl2/MeOH 10:1)

Sources & evidence

ORD record
ord-755a9f9466c346a49ec00e9370272a23
Source dataset
uspto-grants-2006_09
Patent number
US07105523B2

Reaction notes

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