Sodium borohydride → HCID 178508617, compound

HRID 432231Notes

Reaction equation

HRID 432231 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:24]3[CH2:27][C:26](=[O:28])[CH2:25]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:3]=12.[BH4-].[Na+]>O1CCCC1.C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:24]3[CH2:25][C@H:26]([OH:28])[CH2:27]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22346823HCID 22346823, compound

Product 1

HCID 178508617HCID 178508617, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclobutanone (0.208 g, 0.00056 mol) in tetrahydrofuran (10 mL) and absolute ethanol (5 mL) was reacted with sodium borohydride (0.021 g, 0.00056 mol) at room temperature for four hours. Added water (5 mL) and extracted with ethyl acetate (3×15 mL). The combined organics were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica using dichloromethane/methanol (98:2). The solvent was removed in vacuo to give cis 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclobutanol (0.090 g, 0.00024 mol) as a white solid.

Workup

  1. extractionAdded water (5 mL) and extracted with ethyl acetate (3×15 mL)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by flash column chromatography on silica
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aa4068afeb1f47219f3d9cc4e09d08f6
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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