4-Cyclopropyl-6-methyl-2-pyrimidinamine → N-(3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-cyclopropyl-6-methylpyrimidin-2-yl)urea

HRID 1638891Notes

Reaction equation

HRID 1638891 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:19])=[O:18].[NH2:20][C:21]1[N:26]=[C:25]([CH:27]2[CH2:29][CH2:28]2)[CH:24]=[C:23]([CH3:30])[N:22]=1>O1CCOCC1>[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([NH:15][C:16]([NH:20][C:21]3[N:26]=[C:25]([CH:27]4[CH2:29][CH2:28]4)[CH:24]=[C:23]([CH3:30])[N:22]=3)=[O:17])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 136726584-Cyclopropyl-6-methyl-2-pyrimidinamineHCID 198393593,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonylisocyanate

Product 1

HCID 19839356N-(3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-cyclopropyl-6-methylpyrimidin-2-yl)urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

66.5 ml of a 10.78% solution of 3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl isocyanate in dioxane is added dropwise over 5 minutes at room temperature to a mixture of 3.72 g of 2-amino-4-cyclopropyl-6-methylpyrimidine in 100 ml of absolute dioxane. The mixture is stirred for a further 18 hours and then concentrated by evaporation. The residue is crystallised by trituration with a 1:2 mixture of ethyl acetate and petroleum, affording 11.2 g of N-(3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-cyclopropyl-6-methylpyrimidin-2-yl)urea with a melting point of 216°-217° C.

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue is crystallised by trituration with a 1:2 mixture of ethyl acetate and petroleum

Sources & evidence

ORD record
ord-25a18823a14c4bcc834fb0d47c9f59d2
Source dataset
uspto-grants-1989_11
Patent number
US04881964

Reaction notes

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