Water → 5-methoxy-2-sulfanyl-4-pyrimidinol

HRID 480028Notes

Reaction equation

HRID 480028 reaction equation
C1C=C2C=CC=C(/C=C/C3C=C[N+](C[CH2:20][OH:21])=CC=3)C2=CC=1.[Br-].[NH2:23][C:24]([NH2:26])=[S:25].O.CN1C[CH2:32][CH2:31][C:30]1=[O:34]>>[CH3:20][O:21][C:31]1[C:30](=[O:34])[NH:23][C:24](=[S:25])[NH:26][CH:32]=1

Participants

5

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 2723790ThioureaHCID 6441477N-(2-hydroxyethyl)-4-(beta-(1-naphthylvinyl)pyridinium bromide)

Product 1

HCID 27637595-methoxy-2-sulfanyl-4-pyrimidinol

Procedure

Intermediate B111 (2.64 g, 1 equiv) and thiourea (2.42 g, 4 equiv) in 1-methyl-2-pyrrolidinone (40 ml) was heated to 180° C. for 2 hours. After cooling the mixture was treated with water and the resultant solid collected by filtration. This solid was applied to a column (silica, 2% methanol/dichloromethane) to afford the title compound as a colourless solid (0.169 g). 1H-NMR (CDCl3) δ 1.22 (3H, t), 4.21 (2H, q), 5.53 (2H,br s), 7.46 (1H, t), 7.53 (1H, d), 7.81 (1H, dt), 8.07 (1H, dd).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationthe resultant solid collected by filtration

Sources & evidence

ORD record
ord-e946e80881674f1abe35cd1dad0faf7f
Source dataset
uspto-grants-2003_11
Patent number
US06649619B1

Reaction notes

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