(2-Chloropyrimidin-4-yl)(cyclopropyl)methanone → 1-(2-Chloropyrimidin-4-yl)-1-cyclopropylethanol

HRID 1039926Notes

Reaction equation

HRID 1039926 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.[CH3:13][Mg]Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([CH:10]2[CH2:11][CH2:12]2)([OH:9])[CH3:13])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 77231065(2-Chloropyrimidin-4-yl)(cyclopropyl)methanoneHCID 178418332HCID 178418332, compound

Product 1

HCID 772310641-(2-Chloropyrimidin-4-yl)-1-cyclopropylethanolYield 60.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-chloropyrimidin-4-yl)(cyclopropyl)methanone (175 mg, 0.958 mmol) in THF (3 mL) at −78° C. under a nitrogen atmosphere was added methyl magnesium chloride (3.0 M in diethyl ether, 0.380 mL, 1.15 mmol) dropwise. The solution was warmed to room temperature and stirred for an additional 30 min. The solution was diluted with EtOAc, washed with brine, dried with MgSO4, filtered, and concentrated to dryness to afford 1-(2-chloropyrimidin-4-yl)-1-cyclopropylethanol (115 mg, 0.579 mmol, 60% yield). MS ESI: [M+H]+ m/z 199.1. 1H NMR (500 MHz, CDCl3) δ 8.60 (d, J=5.2, 1H), 7.43 (d, J=5.2, 1H), 3.43 (s, 1H), 1.52 (s, 3H), 1.26 (m, 1H), 0.60 (m, 1H), 0.50 (m, 1H), 0.40 (m, 1H), 0.30 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-0c474cc456f94917a942c12f16407ef9
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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