Water → HCID 45073367, compound

HRID 729642Notes

Reaction equation

HRID 729642 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×2) 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×2)
  4. customdried

Sources & evidence

ORD record
ord-01ba52efda9545e78887a70d2b4602f8
Source dataset
uspto-grants-2009_09
Patent number
US07582643B2

Reaction notes

Loading…