2,4-Diamino-6-chloropyrimidine → HCID 13914697, compound

HRID 1789122Notes

Reaction equation

HRID 1789122 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])([O:12][CH3:13])=[O:11]>C(#N)C>[NH2:8][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:10]([O:12][CH3:13])=[O:11])(=[O:22])=[O:21])=[O:25])[N:7]=1

Participants

4

Reactant 2

HCID 674322,4-Diamino-6-chloropyrimidineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 13914697HCID 13914697, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a warmed mixture containing 1.4 g (0.01 mole) 2,4-diamino-6-chloropyrimidine in 50 ml acetonitrile is added 2.4 g (0.01 mole) 2-carbomethoxybenzenesulfonylisocyanate. The reaction mixture was stirred at room temperature for four days. The reaction mixture was filtered and the precipitate washed with ether. The filtered solid was air dried and purified in the following manner. To an aqueous suspension of the reaction mixture was added n-propylamine and the aqueous mixture filtered. The resultant clear solution was carefully acidified with concentrated HCl to pH=1-2. The mixture was filtered, washed with ether and air dried to yield a white solid, m.p. 170°-172° C. The infrared spectrums showed characteristic absorption bands at 1740, 1700 cm-1. The NMR and mass spectral data are consistent for the desired product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate washed with ether
  3. customdried
  4. custompurified in the following manner
  5. additionTo an aqueous suspension of the reaction mixture
  6. additionwas added n-propylamine
  7. filtrationthe aqueous mixture filtered
  8. filtrationThe mixture was filtered
  9. washwashed with ether and air
  10. customdried
  11. customto yield a white solid, m.p. 170°-172° C
  12. customabsorption bands at 1740, 1700 cm-1

Sources & evidence

ORD record
ord-0c0178a0dfca4667947a0499d672e7af
Source dataset
uspto-grants-1987_08
Patent number
US04687506

Reaction notes

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