2-Amino-4,6-dimethyl pyrimidine → HCID 13374049, compound

HRID 2418655Notes

Reaction equation

HRID 2418655 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].[Cl:17][C:18]([Cl:27])([Cl:26])[C:19]([C:21]1[NH:22][CH:23]=[CH:24][CH:25]=1)=[O:20].[Cl-].[Al+3].[Cl-].[Cl-]>C[N+]([O-])=O.C(Cl)Cl.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:23]2[NH:22][C:21]([C:19](=[O:20])[C:18]([Cl:27])([Cl:26])[Cl:17])=[CH:25][CH:24]=2)(=[O:13])=[O:12])=[O:16])[N:3]=1

Participants

8

Reactant 4

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13374049HCID 13374049, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent2×

Procedure

To a stirred suspension of 2.59 g (0.021 mol) of 2-amino-4,6-dimethylpyrimidine in 60 ml dry CH3NO2 at -10° was added dropwise, via syringe, under nitrogen, 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature below 5°. The resulting clear solution was stirred 0.5 hour at -5°, then treated dropwise with a solution of 4.46 g (0.021 mole) of 2-trichloroacetyl-1H-pyrrole in 30 ml dry CH3NO2. Upon completion of the addition, 2.95 g (0.022 mole) of aluminum (III) chloride was added in one portion and the reaction mixture stirred 1.5 hour at ambient temperatures followed by 0.5 hour under reflux. The cool solution was poured into H2O, diluted with CH2Cl2 and the layers separated. A precipitate was present in the aqueous layer and was collected by filtration and washed well with water. The organic solution was washed with H2O, dried over MgSO4, evaporated and triturated with CH2Cl2 to afford a second crop of product. Total yield of product was 2.45 g of a tan solid, m.p. 215°-218° (d). The infrared spectrum of the product included absorptions at 3230 (NH), 1692 (C=O), 1340 and 1160 cm-1 (SO2).

Workup

  1. additionwas added dropwise, via syringe, under nitrogen
  2. additionwas added in one portion
  3. stirringthe reaction mixture stirred 1.5 hour at ambient temperatures
  4. waitfollowed by 0.5 hour
  5. temperatureunder reflux
  6. customthe layers separated
  7. filtrationwas collected by filtration
  8. washwashed well with water
  9. washThe organic solution was washed with H2O
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customtriturated with CH2Cl2
  13. customto afford a second crop of product

Sources & evidence

ORD record
ord-c8f36840f7054e9ab6cec94a1a84174e
Source dataset
uspto-grants-1984_09
Patent number
US04473394

Reaction notes

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