Methanol → 5-Methoxy-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

HRID 1245421Notes

Reaction equation

HRID 1245421 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([O:11]COC)(=O)[CH2:6][C:7]([O-:9])=O.[Na].[CH3:16][OH:17]>>[CH3:16][O:17][CH:6]1[C:5](=[O:11])[NH:4][C:2](=[S:3])[NH:1][C:7]1=[O:9]

Participants

5

Reactant 4

HCID 887MethanolHCID 2723790ThioureaHCID 5360545SodiumHCID 21912471Methoxymethyl malonate

Product 1

HCID 219124765-Methoxy-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Procedure

Thiourea (24 g) and methoxymethyl malonate (34 g) was added to a solution of sodium (12 g) in methanol and the mixture heated under reflux for 10 h. The methanol was evaporated under reduced pressure, water (500 ml) added and extracted with ether. The aqueous layer was acidified to pH1 with conc. hydrochloric acid, evaporated to ˜200 ml and the precipitate filtered and dried. Yield 23 g

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 10 h
  3. customThe methanol was evaporated under reduced pressure, water (500 ml)
  4. additionadded
  5. extractionextracted with ether
  6. customevaporated to ˜200 ml
  7. filtrationthe precipitate filtered
  8. customdried

Sources & evidence

ORD record
ord-15a4e578ca8749c0905cd438242714ed
Source dataset
uspto-grants-2006_10
Patent number
US07125881B2

Reaction notes

Loading…