Hydrogen Sulfide → Ethyl 4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxylate

HRID 1651526Notes

Reaction equation

HRID 1651526 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:13][C:12]([CH3:14])=[N:11][C:10]([CH3:15])=[C:9]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1.[S].S>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:10]([CH3:15])[N:11]=[C:12]([CH3:14])[N:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 5362487SulfurHCID 178469227HCID 178469227, compound

Product 1

HCID 14513884Ethyl 4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxylateYield 64.8%

Procedure

Ethyl 6-(4-fluorophenyl)-1,6-dihydro-2,4-dimethyl-5-pyrimidinecarboxylate (75.7 g, 0.274 mol) and 9.67 g (0.3 mol) of powdered sulfur were heated together at 130°-150° C. for three and one-half hours. After hydrogen sulfide evolution had ceased, the melt was cooled to room temperature and flash chromatographed on silica gel, eluting with 10% ethyl acetate/hexane, to yield 48.7 g of ethyl 4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxylate.

Workup

  1. customflash chromatographed on silica gel
  2. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-23807ffcd6a844ed99b5d1b6fe8e59f0
Source dataset
uspto-grants-1990_05
Patent number
US04929620

Reaction notes

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