1,4-Dioxane → N-(2-methoxycarbonylphenyl-sulfonyl)-N'-[4-methoxy-6-(pyridin-2-ylthiomethyl)-pyrimidin-2-yl]-urea

HRID 981743Notes

Reaction equation

HRID 981743 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([N:31]=[C:32]=[O:33])(=[O:30])=[O:29])=[O:21].O1CCOCC1>C(#N)C>[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH:31][C:32]([NH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1)=[O:33])(=[O:29])=[O:30])=[O:21]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 200708422-Amino-4-methoxy-6-(pyridin-2-ylthiomethyl)pyrimidine

Product 1

HCID 54268146N-(2-methoxycarbonylphenyl-sulfonyl)-N'-[4-methoxy-6-(pyridin-2-ylthiomethyl)-pyrimidin-2-yl]-urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.0 g of 2-amino-4-methoxy-6-(pyridin-2-ylthiomethyl)pyrimidine and 6.8 g of 2-methoxycarbonylphenylsulfonylisocyanate are stirred in 50 ml of abs. acetonitrile for 2 hours at 20°-25° C. The turbid solution is filtered, and the solvent evaporated off in vacuo. The residue is crystallised from dioxane to thus obtain 5.5 g (37% of theory) of N-(2-methoxycarbonylphenyl-sulfonyl)-N'-[4-methoxy-6-(pyridin-2-ylthiomethyl)-pyrimidin-2-yl]urea, which crystallises with 0.5 mol of dioxane, m.p. 175°-181° C.

Workup

  1. filtrationThe turbid solution is filtered
  2. customthe solvent evaporated off in vacuo
  3. customThe residue is crystallised from dioxane to thus obtain 5.5 g (37% of theory) of N-(2-methoxycarbonylphenyl-sulfonyl)-N'-[4-methoxy-6-(pyridin-2-ylthiomethyl)-pyrimidin-2-yl]urea, which

Sources & evidence

ORD record
ord-198a45c2f342493eb45e9b4cfeb1ba14
Source dataset
uspto-grants-1991_02
Patent number
US04992549

Reaction notes

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