4-Methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine → HCID 13068372, compound

HRID 1759136Notes

Reaction equation

HRID 1759136 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.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])([O-:14])=[O:13]>C(Cl)Cl>[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([NH:11][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])(=[O:22])=[O:23])=[O:26])[N:3]=1

Participants

4

Reactant 2

HCID 9042124-Methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amineHCID 111388842-Nitrobenzenesulfonyl isocyanate

Product 1

HCID 13068372HCID 13068372, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dry, stirred solution of 10 g of 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine in 800 ml of methylene chloride at ambient temperature and pressure was added 14.9 g of 2-nitrobenzenesulfonylisocyanate. The resulting mixture was stirred at reflux temperature (42°) for 2 hours after which the methylene chloride was removed under reduced pressure. The resulting solid was triturated with methanol or 1-chlorobutane and filtered to yield 15 g of N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzene-sulfonamide, m.p. 202°-205°. The product showed characteristic absorption bands in the infrared spectrum at 1675 cm-1 and at 1.7, 3.2 and 7.7 to 8.5 ppms by nuclear magnetic resonance spectrum (60 MHz), indicating the title compound.

Workup

  1. customwas removed under reduced pressure
  2. customThe resulting solid was triturated with methanol or 1-chlorobutane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b13bcfaa47984d9a9ee448544d5c14c7
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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