2-Methyl-2-thiopseudourea sulfate → Methyl 2-(Methylthio)pyrimidine-5-carboxylate

HRID 1867168Notes

Reaction equation

HRID 1867168 reaction equation
[Na].[CH3:2][O:3][CH:4]([O:12]C)[C:5]([C:8](OC)=O)=[CH:6]O.S(O)(O)(=O)=O.[CH3:19][S:20][C:21](=[NH:23])[NH2:22]>CO.C(OCC)(=O)C>[CH3:19][S:20][C:21]1[N:23]=[CH:8][C:5]([C:4]([O:3][CH3:2])=[O:12])=[CH:6][N:22]=1

Participants

6

Reactant 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 5360545SodiumHCID 591179393,3-Dimethoxy-2-methoxycarbonylpropen-1-ol

Product 1

HCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (5.0 g, 25 mmol), 2-methyl-2-thiopseudourea sulfate (3.5 g, 25 mmol) in anhydrous methanol (25 mL) was refluxed for 3 hours under anhydrous conditions. The reaction mixture was cooled and diluted with ethyl acetate. The reaction mixture was filtered and the residue was washed with ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography (silica gel) using 25% ethyl acetate in hexane to afford the desired product (3.5 g, 75%) as a white powder. 1H-NMR (d6-DMSO, 400 MHz) δ 9.0 (s, 2H), 3.92 (s, 3H), 2.58 (s, 3H); ES-HRMS m/z 185.041 (M+H C7H8N2O2S requires 185.0379).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-9e94f34266124f1e8b0780dcb4d99471
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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