2-Pyrimidinamine, 5-chloro- → Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate

HRID 66442Notes

Reaction equation

HRID 66442 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[N:9]([S:12]([C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[C:10]=[O:11]>C(Cl)Cl>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([NH:1][C:10]([NH:9][S:12]([C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[O:11])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 794792-Pyrimidinamine, 5-chloro-HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 13038386Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-chloropyrimidine (1.3 g) was suspended in 20 ml of methylene chloride and to this was added with stirring 2.4 g of methyl 2-(isocyanatosulfonyl)-benzoate. After stirring for three hours at ambient temperature, the desired product, 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester, which had precipitated as a white solid, was filtered off. It melted at 217°-221° and showed peaks in the nuclear magnetic resonance spectrum (trifluoroacetic acid solvent) at 4.0δ (singlet) for OCH3, 9.0δ for H at the 4- and 6-position of the hetero ring and at 7.9δ and 8.2-8.4δ for aromatic H, consistent for the above-named product.

Workup

  1. additionto this was added
  2. customthe desired product, 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester, which had precipitated as a white solid
  3. filtrationwas filtered off

Sources & evidence

ORD record
ord-b66172d0653b4d7f8a96f631319b5674
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Reaction notes

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