Sodium borohydride → (2-Chloropyrimidin-4-yl)(cyclopropyl)methanol

HRID 410436Notes

Reaction equation

HRID 410436 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH:10]2[CH2:11][CH2:12]2)[OH:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 77231065(2-Chloropyrimidin-4-yl)(cyclopropyl)methanone

Product 1

HCID 77231063(2-Chloropyrimidin-4-yl)(cyclopropyl)methanolYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-chloropyrimidin-4-yl)(cyclopropyl)methanone (150 mg, 0.821 mmol) in MeOH (3 mL) at 0° C. was added sodium borohydride (31 mg, 0.821 mmol) and stirred for 30 min: The solution was diluted with EtOAc, washed with brine, dried with MgSO4, filtered, and concentrated to dryness to afford (2-chloropyrimidin-4-yl)(cyclopropyl)methanol (150 mg, 0.812 mmol, 99% yield). MS ESI: [M+H]+m/z 185.1. 1H NMR (500 MHz, CDCl3) δ 8.60 (d, J=4.0, 1H), 7.41 (d, J=4.0, 1H), 4.12 (d, J=7.9, 1H), 1.12 (m, 1H), 0.64 (m, 2H), 0.56 (m,

Workup

  1. washwashed with brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7f010164643c4b0b815e86a05522e41b
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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