Methanol → HCID 57477899, compound

HRID 1817607Notes

Reaction equation

HRID 1817607 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH3:26])[CH2:22][CH:23]=[O:24])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.CO.[BH4-].[Na+]>O>[CH3:27][Si:2]([CH3:1])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH3:26])[CH2:22][CH2:23][OH:24])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 574778983-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanal

Product 1

HCID 57477899HCID 57477899, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanal (50 mg, 0.0001 mol) in methanol (2 mL, 0.05 mol) was treated with sodium tetrahydroborate (8 mg, 0.0002 mol). The mixture was stirred at room temperature for 1 h, and then water was added and the product was extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give the desired product as an oil. LC/MS (M+H)+: m/z=402.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d09b32535c564e9ab50e7f45c92de778
Source dataset
uspto-grants-2009_10
Patent number
US07598257B2

Reaction notes

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