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

HRID 1039927Notes

Reaction equation

HRID 1039927 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, 2H).

Workup

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

Sources & evidence

ORD record
ord-6e26f318d6dc4be9ba8baa3f96e2faab
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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