Sodium methanethiolate → 1-(4-Isopropylamino-2-methylsulphanyl-pyrimidin-5-yl)-ethanone

HRID 475323Notes

Reaction equation

HRID 475323 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12](=[O:14])[CH3:13])=[CH:4][N:3]=1.[CH3:15][S-:16].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH:9]([NH:8][C:6]1[C:5]([C:12](=[O:14])[CH3:13])=[CH:4][N:3]=[C:2]([S:16][CH3:15])[N:7]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 574611371-(2-Chloro-4-isopropylaminopyrimidin-5-yl)-ethanone

Product 1

HCID 574611381-(4-Isopropylamino-2-methylsulphanyl-pyrimidin-5-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

1-(2-chloro-4-isopropylamino-pyrimidin-5-yl)-ethanone (11.1 g, 0.052 mol) and sodium thiomethoxide (5.75 g, 0.078 mol) are taken up in 100 mL dioxane and stirred for 16 h at 20° C. The solvent is eliminated in vacuo, the residue is taken up in ethyl acetate and extracted 2× with water. The organic phase is dried, the solvent is eliminated in vacuo and 1-(4-isopropylamino-2-methylsulphanyl-pyrimidin-5-yl)-ethanone (HPLC-MS: tRet.=1.82 min, MS(M+H)+=226; method FECB3) is obtained.

Workup

  1. extractionextracted 2× with water
  2. customThe organic phase is dried

Sources & evidence

ORD record
ord-4a5c0785809c4dd29db6dfe98656c3a2
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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