Sodium borohydride → HCID 86672123, compound

HRID 82274Notes

Reaction equation

HRID 82274 reaction equation
C[O:2][C:3]([C:5]1([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[CH:16][C:11]=3[CH:10]=[CH:9]2)[CH2:7][CH2:6]1)=O.[BH4-].[Na+]>C(O)C>[N:13]1[C:12]2[N:8]([C:5]3([CH2:3][OH:2])[CH2:6][CH2:7]3)[CH:9]=[CH:10][C:11]=2[CH:16]=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 708174621-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 86672123HCID 86672123, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl ester (Preparation 246, 610 mg, 2.80 mmol) in ethanol (15 mL) was added sodium borohydride (318.7 mg, 8.42 mmol) and the mixture heated to reflux for 16 hours. The reaction mixture was quenched with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with water (5 mL), brine (5 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2) to afford the title compound as a light yellow solid in 47% yield, 250 mg.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. customThe reaction mixture was quenched with water (5 mL)
  4. extractionextracted with EtOAc (3×10 mL)
  5. washThe combined organic layers were washed with water (5 mL), brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2)

Sources & evidence

ORD record
ord-b852999f622e46e1b0373ad9d7a7b33b
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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