2-Amino-4,6-dimethyl pyrimidine → HCID 13090871, compound

HRID 637602Notes

Reaction equation

HRID 637602 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[NH:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([O:24][CH3:25])=[O:23].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:15]([NH:14][S:11]([C:20]2[CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[NH:17][CH:21]=2)(=[O:13])=[O:12])=[O:16])[N:3]=1

Participants

7

Reactant 4

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13090871HCID 13090871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent2×

Procedure

To a stirred suspension of 2.58 g (0.021 mol) of 2-amino-4,6-dimethylpyrimidine in 75 ml dry nitromethane at -10° was added dropwise, via syringe, under nitrogen, 2.0 ml (0.023 mol) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 0°. The resulting clear solution was stirred 0.5 hour at -5° to -10°, then treated dropwise with a solution of 2.29 g (0.021 mole) of methyl pyrrole-2-carboxylate in 25 ml dry nitromethane. Upon completion of the addition, 2.95 gm (0.022 mole) of aluminum (III) chloride was added in one portion. The reaction mixture was heated at reflux for 2 hours, then allowed to stand overnight at ambient temperatures. The mixture was poured into 300 ml H2O and the two phase system extracted with three portions of CH2Cl2. The organic solutions were washed with water, dried over MgSO4 and evaporated to a tan foam which was triturated with minimal CH2Cl2 to afford the product as a white solid, m.p. 202°-204°.

Workup

  1. additionwas added dropwise, via syringe, under nitrogen
  2. additionwas added in one portion
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 2 hours
  5. waitto stand overnight at ambient temperatures
  6. extractionthe two phase system extracted with three portions of CH2Cl2
  7. washThe organic solutions were washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated to a tan foam which
  10. customwas triturated with minimal CH2Cl2

Sources & evidence

ORD record
ord-4cd5e9713feb4787ada0d5e6e2bff560
Source dataset
uspto-grants-1985_12
Patent number
US04557752

Reaction notes

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