Methyl formate → 5-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

HRID 411286Notes

Reaction equation

HRID 411286 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]CC)=O)=[CH:11][N:10]=1.[CH:22](OC)=O.[NH2:26][C:27]([NH2:29])=[S:28]>C1COCC1.CCOCC.CC(O)C>[CH3:7][O:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][C:16]2[C:17](=[O:19])[NH:26][C:27](=[S:28])[NH:29][CH:22]=2)=[CH:13][N:14]=1

Participants

8

Reactant 4

HCID 7865Methyl formateHCID 2723790ThioureaHCID 21936233Ethyl 3-(2-methoxypyrimidin-5-yl)propionateHCID 23665647Potassium tert-butoxide

Product 1

HCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of potassium t-butoxide (7.83 g, 0.07 mol) in anhydrous THF (60 ml) was added dropwise with stirring under argon over 1 hour to a solution of ethyl 3-(2-methoxypyrimidin-5-yl)propionate (5.87 g, 0.028 mol) and methyl formate (3.6 ml, 0.059 mol) in anhydrous ether (70 ml). After stirring for 16 h, the solvents were evaporated, thiourea (4.25 g, 0.056 mol) and propan-2-ol (80 ml) added and the mixture refluxed for 5 h. The solvent was evaporated and the residue dissolved in water, extracted twice with ether and acidified to pH 4.5 with acetic acid. The solid which precipitated was filtered, washed well with water and dried, yield 5.57 g (80%). 1H-NMR (d6-DMSO) δ3.47 (2H, s), 3.85 (3H, s), 7.43 (1H, s), 8.48 (2H, s), 12.25 (1H, br s), 12.46 (1H, br s); MS (APCI+) found (M+H)=251; C10H10N4O2S requires 250.

Workup

  1. customthe solvents were evaporated
  2. temperaturethe mixture refluxed for 5 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionextracted twice with ether
  6. customThe solid which precipitated
  7. filtrationwas filtered
  8. washwashed well with water
  9. customdried

Sources & evidence

ORD record
ord-24fb2ec41368418e88d78042f0d9af3d
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

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