Sodium Chloride → 2-Cyclopropylmethoxy-pyrimidin-4-ylamine

HRID 1786134Notes

Reaction equation

HRID 1786134 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=1.[Na+].[Cl-]>CN(C=O)C.O>[CH:1]1([CH2:4][O:5][C:11]2[N:10]=[C:9]([NH2:8])[CH:14]=[CH:13][N:12]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 3457522-Chloro-4-aminopyrimidine

Product 1

HCID 671775362-Cyclopropylmethoxy-pyrimidin-4-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Cyclopropylmethanol (724 mg) was dissolved in DMF (4 mL) and treated with sodium hydride (401 mg, 60% in mineral oil) at 0° C. for 30 minutes. Then, a solution of 4-amino-2-chloro-pyrimidine (260 mg, CAS 7461-50-9 or made according to J. Am. Chem. Soc. 1930, 52, 1152-1157) in DMF (4 mL) was added drop by drop. The mixture was stirred at room temperature for 1 hour and then allowed to stir at 50° C. over night. The mixture was poured into water and the mixture was saturated with NaCl. The aqueous solution was then extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in heptane as an eluant. The desired product was obtained as a light yellow oil (169 mg). MS (EI): 166.2 (M+H+).

Workup

  1. stirringto stir at 50° C. over night
  2. extractionThe aqueous solution was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in heptane as an eluant

Sources & evidence

ORD record
ord-234de0d245f14da2a7db17fad5bb1f8a
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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