Water → HCID 45073367, compound

HRID 563865Notes

Reaction equation

HRID 563865 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[NH:10])[NH2:9])[CH:5]=[CH:6][CH:7]=1.CN(C)[CH:13]=[O:14].[OH2:16]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:5][C:4]([C:8]([O:14][CH3:13])=[O:16])=[CH:3][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 36393453-fluorobenzenecarboximidamide

Product 1

HCID 45073367HCID 45073367, compoundYield 59%

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3,3-dimethoxypropionate (304 g, 2.05 mol) in dimethoxyethane (1.5 L) was added methyl formate (580 g, 9.44 mol). Sodium hydride (98.5 g, 60% suspension in mineral oil, 2.46 mol) was added portion-wise and the mixture was stirred at 50° C. for 5 hours and then at room temperature overnight. Diethyl ether (1.5 L) was added and the reaction was filtered under an atmosphere of nitrogen. The solid residue was washed with diethyl ether (300 mL ×2) and dried to give 200 g (68.9%) of [methyl-2-(dimethoxymethyl)-3-(hydroxyl-kappaO)acrylatato]sodium. A mixture of this compound (63.5 g, 0.32 mol), 3-fluorobenzenecarboximidamide (38 g, 0.27 mol) and dimethylformamide (400 mL) was heated at 100° C. for 2 h. After this time the reaction was cooled to room temperature and water (400 mL) was added. The reaction was filtered and the residue was washed with water (100 mL x2) and dried to give 37 g (yield 59%) of methyl 2-(3-fluorophenyl)pyrimidine-5-carboxylate.

Workup

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. filtrationThe reaction was filtered
  3. washthe residue was washed with water (100 mL x2)
  4. customdried

Sources & evidence

ORD record
ord-30ca6259ce3c49308351423486eb3617
Source dataset
uspto-grants-2011_11
Patent number
US08067589B2

Reaction notes

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