Dichloromethane → 2-Chloro-N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]pyridine-3-sulfonamide

HRID 1759138Notes

Reaction equation

HRID 1759138 reaction equation
[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([NH2:11])[N:3]=1.ClC1N([S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20])C=CC=N1.[CH2:25]([Cl:27])Cl>>[Cl:27][C:25]1[C:10]([S:19]([NH:22][C:23]([NH:11][C:4]2[N:3]=[C:2]([CH3:1])[C:7]3[CH2:8][CH2:9][CH2:10][C:6]=3[N:5]=2)=[O:24])(=[O:20])=[O:21])=[CH:6][CH:7]=[CH:2][N:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 9042124-Methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amineHCID 205321432-Chloropyrimidine-3-sulfonylisocyanate

Product 1

HCID 205321492-Chloro-N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]pyridine-3-sulfonamide

Procedure

To a dry, stirred solution of 7.5 g of 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine in 200 ml of methylene chloride at ambient temperature and pressure is added 13 g of 2-chloropyrimidine-3-sulfonylisocyanate. The resulting mixture is stirred at reflux for 2 hours and then concentrated at reduced pressure. The residue is triturated with 1-chlorobutane and filtered to yield the desired solid product.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated at reduced pressure
  3. customThe residue is triturated with 1-chlorobutane
  4. filtrationfiltered
  5. customto yield the desired solid product

Sources & evidence

ORD record
ord-daf8c73518e1433d888d201b692a4462
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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