Hydrochloric Acid → Methyl 4-methyl-2-(methylthio)-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 516026

Reaction equation

HRID 516026 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=1.[CH3:21][S-:22].[Na+].Cl>CN(C=O)C>[CH3:8][C:6]1[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=[C:2]([S:22][CH3:21])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 58317549Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

Product 1

HCID 58317603Methyl 4-methyl-2-(methylthio)-6-(m-tolylamino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate (0.078 g, 0.267 mmol) was dissolved in DMF (3 mL). Sodium thiomethoxide (0.019 g, 0.267 mmol) was added and the reaction mixture was allowed to stir at RT for 1 h. The reaction mixture was poured onto ice. The pH was adjusted to 7 with 1 N HCl. The title compound was isolated as a yellow solid by vacuum filtration (72.8 mg, 90%). [M+H] calc'd for C15H17N3O2S, 304; found, 304.

Workup

  1. additionThe reaction mixture was poured onto ice

Sources & evidence

ORD record
ord-63c11bcdfab84bda8a754d1eada85c4f
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Linked notes

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