Gamma-Butyrolactone → 5-(2-hydroxyethyl)-2-thiouracil

HRID 539855Notes

Reaction equation

HRID 539855 reaction equation
C(OCC)=O.[C:6]1(=[O:11])[O:10][CH2:9][CH2:8][CH2:7]1.[CH3:12]C(C)([O-])C.[K+].[NH2:18][C:19]([NH2:21])=[S:20]>CCOCC.O1CCCC1.CC(O)C>[OH:10][CH2:9][CH2:8][C:7]1[C:6](=[O:11])[NH:18][C:19](=[S:20])[NH:21][CH:12]=1

Participants

8

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 8025Ethyl formateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

Product 1

HCID 36146775-(2-hydroxyethyl)-2-thiouracil

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl formate (33.1 ml, 2.1 equiv) and γ-butyrolactone (15 ml, 1 equiv) in ether (400 ml) was added dropwise with stirring to a solution of potassium t-butoxide (52.5 g, 2.4 equiv) in tetrahydrofuran (400 ml). The mixture was allowed to warm to room temperature, and stirred overnight. The solvent was removed in vacuo, 2-propanol (600 ml) and thiourea (29.7 g, 2 equiv) were added, and the mixture was heated to reflux for 5 h. After cooling to room temperature, the precipitate was filtered off, dissolved in water (500 ml), and washed twice with ether. The aqueous solution was acidified to pH5.5 with acetic acid, and the resulting precipitate was filtered off, washed thoroughly with water, and dried in vacuo; yield 23.85 g. 1H-NMR (d6-DMSO) δ 2.36 (2H, t), 3.47 (2H, m), 4.57 (1H, m), 7.24 (1H, s), 12.2 & 12.4 (each 1H, br s); MS (APCI−) found (M−H)=171; C6H8N2O2S requires 172.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 h
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was filtered off
  6. dissolutiondissolved in water (500 ml)
  7. washwashed twice with ether
  8. filtrationthe resulting precipitate was filtered off
  9. washwashed thoroughly with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-708f99d0e44144b38e79df2e6dd543db
Source dataset
uspto-grants-2014_10
Patent number
US08871775B2

Reaction notes

Loading…