2-Methyl-2-thiopseudourea → 2-Methylthio-thiopyranopyrimidine

HRID 1903298Notes

Reaction equation

HRID 1903298 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][S:4][CH:3]1[C:8](OCC)=O.[CH3:13][S:14][C:15](=[NH:17])[NH2:16].[OH-].[K+].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+].[H-].[Na+].C[O-].[Na+].[O-]CC.[Na+]>CN(C)C=O.C(O)(C)C.C(O)C.CO>[CH3:13][S:14][C:15]1[N:17]=[CH:8][C:3]2[S:4][CH2:5][CH:6]=[CH:7][C:2]=2[N:16]=1

Participants

14

Reactant 9

HCID 51422-Methyl-2-thiopseudoureaHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 10942334Sodium MethoxideHCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate

Product 1

HCID 705136292-Methylthio-thiopyranopyrimidine

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

According to the above reaction scheme, ethyl 3-oxotetrahydrothiopyran-2-carboxylate is reacted with S-methylisothiourea in the presence of a basic catalyst such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, sodium methoxide, sodium ethoxide and the like, in a solvent such as methanol, ethanol, isopropyl alcohol, N,N-dimethylformamide to produce a 2-methylthio-thiopyranopyrimidine compound (V), and the resulting compound (V) is then heated under acidic conditions, preferably in a mixture of acetic acid and water to produce a 2,4-dihydroxythiopyranopyrimidine compound (VI). Subsequently, the resulting 2,4-dihydroxy compound (VI) is reacted with phosphorus oxychloride in the absence or presence of a tertiary amine such as N,N-dimethylaniline, N,N-diethylaniline and the like to obtain the starting material of the formula (III).

Sources & evidence

ORD record
ord-cffaad7538464124ad2b1ed4c08691ed
Source dataset
uspto-grants-1984_03
Patent number
US04435566

Reaction notes

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