Water → 2-Chloro-4-(cyclopropylmethoxy)-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine
Reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[C:11]([CH2:16][O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:10]=1.O>C1COCC1>[Cl:8][C:9]1[N:14]=[C:13]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)[CH:12]=[C:11]([CH2:16][O:17][CH2:18][C:19]([F:22])([F:20])[F:21])[N:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydride (19.0 mg, 0.46 mmol) was added to a solution of cyclopropylmethanol (0.037 mL, 0.46 mmol) in dry THF (1 mL) at room temperature. The mixture was stirred for 5 minutes and then a solution of 2,4-dichloro-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine (120 mg, 0.46 mmol) in dry THF (1 mL) was added. The reaction was stirred at room temperature for 2.5 hours. Water was added and the mixture was extracted with ethylacetate. The organic phase was washed with water, brine, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with mixtures of 0% to 10% ethyl acetate in heptanes to afford the title compound as a solid, 40 mg, (29%) as yellow solid.
Workup
- stirringThe reaction was stirred at room temperature for 2.5 hours
- extractionthe mixture was extracted with ethylacetate
- washThe organic phase was washed with water, brine
- dry with materialdried over magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by flash chromatography on silica gel
- washeluting with mixtures of 0% to 10% ethyl acetate in heptanes
Sources & evidence
- ORD record
- ord-99a68e4d6adb4e8ab8a115ee8c7c5495
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439904B2
Reaction notes
Loading…