Methanol → HCID 86690478, compound

HRID 1026753Notes

Reaction equation

HRID 1026753 reaction equation
[BH4-].[Li+].CO.[F:5][C:6]([F:26])([F:25])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20](OCC)=[O:21])[CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:26][C:6]([F:5])([F:25])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 86690479HCID 86690479, compound

Product 1

HCID 86690478HCID 86690478, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After lithium borohydride (3.0 M solution in tetrahydrofuran) (0.05 mL) and methanol (0.006 mL) was added dropwise to an ice-cold solution of ethyl 2-[4-(trifluoromethoxy)phenyl]pyrimidine-4-carboxylate (29 mg) in tetrahydrofuran (3.0 mL), the mixture was stirred for 1 hr, then returned to room temperature and stirred for 30 min. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethyl acetate. After washing with 2N hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, the organic phase was separated out. The solvent was distilled off under reduced pressure to afford the title compound (13 mg) as the residue.

Workup

  1. customreturned to room temperature
  2. stirringstirred for 30 min
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washAfter washing with 2N hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  6. customthe organic phase was separated out
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ce52d4887d5e48c2b7ebc726fd71c0e5
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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