Water → HCID 67176601, compound

HRID 1786130Notes

Reaction equation

HRID 1786130 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:5][CH2:4]1.Cl[CH2:7][C:8]1[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][N:9]=1.O>C1COCC1.[H-].[Na+]>[CH:3]1([CH2:2][O:1][CH2:7][C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 75644CyclopropanemethanolHCID 212988272-(Chloromethyl)pyrimidin-4-amine

Product 1

HCID 67176601HCID 67176601, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 24758Sodium hydrideSolvent

Procedure

Hydroxymethylcyclopropane (0.17 g) was dissolved in THF (2 mL) and at 0° C. sodium hydride dispersion (55% in oil, 0.1 g) was added. The mixture was allowed to stir for 30 minutes and subsequently, a solution of 2-chloromethyl-pyrimidin-4-ylamine (0.2 g, Eur. Pat. Appl. EP 61318 A2, 1982; Eur. Pat. Appl. 60094 A2, 1982) in THF (7 mL) was added dropwise. The resulting mixture was heated to reflux for 2 hours, cooled and water was added. The mixture was extracted with ethyl acetate and the organic layers were combined, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (ethyl acetate/methanol 9:1) to give 2-cyclopropylmethoxymethyl-pyrimidin-4-ylamine as colorless solid (54 mg). 1H NMR (δ, CDCl3): 8.22 (d, 1H), 6.32 (d, 1H), 4.98 (br s, 2H), 4.58 (s, 2H), 3.46 (d, 2H), 1.21-1.12 (m, 1H), 0.59-0.53 (m, 2H), 0.27-0.24 (m, 2H). MS (ESI): 180.3 (MH+).

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 2 hours
  4. temperaturecooled
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-9124b9c72cce48b38d8b470124738db6
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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