Sodium borohydride → 3-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propan-1-ol

HRID 2357984Notes

Reaction equation

HRID 2357984 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]=[O:29])[N:11]=1.[BH4-].[Na+]>C(O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH2:28][OH:29])[N:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 588368773-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanal

Product 1

HCID 160488223-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 27 mg (0.07 mmol) of crude 3-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanal 36 (Example 4, Step A) in 4 mL of absolute ethanol was treated with 17 mg (0.4 mmol) of NaBH4. The resulting orange slurry was stirred at room temperature for 2 h. The reaction mixture was quenched with water (10 mL) and concentrated. The residue was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4) to give the title compound 37. 1H-NMR (CD3OD) δ1.96-2.04 (m, 2H), 2.26 (s, 6H), 3.54 (t, J=6.3 Hz, 2H), 4.20 (t, J=6.7 Hz, 2H), 6.99 (dt, J=7.4 Hz, 0.9 Hz, 1H), 7.09-7.17 (m, 3H), 7.30 (t, J=7.6 Hz, 2H), 7.75 (dd, J=8.6 Hz, 0.9 Hz, 2H), 8.09 (s, 1H). Mass Spectrum (ESI) m/e=389.2 (M+1).

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. concentrationconcentrated
  3. extractionThe residue was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4)

Sources & evidence

ORD record
ord-6639db886cc44b6aaede134f0012a3cc
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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