Methyl formate → methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoate

HRID 705952Notes

Reaction equation

HRID 705952 reaction equation
[H-].[Na+].[CH:3]([O:5][CH3:6])=[O:4].[F:7][C:8]([F:22])([F:21])[C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](OC)=[O:18])=[CH:11][N:10]=1>COCCOC>[OH:18]/[CH:17]=[C:16](/[CH2:15][C:12]1[CH:11]=[N:10][C:9]([C:8]([F:22])([F:21])[F:7])=[N:14][CH:13]=1)\[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 21936211Methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate

Product 1

HCID 67953508methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoateYield 82%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of NaH (360 mg, 9.00 mmol) in DME (20 mL) was added a solution of methyl formate (0.254 mL, 4.10 mmol) and methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate (800 mg, 3.42 mmol) in DME (20 mL) at 0° C. The mixture was stirred at room temperature overnight, and quenched with MeOH. Purification via reverse phase flash chromatography afforded the title compound (730 mg, 2.78 mmol, 82% yield) as yellow solid. LCMS: rt=2.03 min, [M+H+]=263.

Workup

  1. customquenched with MeOH
  2. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-518a7027ec58417a86ff8152975c661b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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