2-Amino-4,6-dimethyl pyrimidine → 1-(2-cyanoethyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1H-pyrrole-2-sulfonamide

HRID 2418653Notes

Reaction equation

HRID 2418653 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].[C:17]([CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1)#[N:18].[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1.O>[C:17]([CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:11]([NH:14][C:15]([NH:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1)=[O:16])(=[O:13])=[O:12])#[N:18]

Participants

7

Reactant 4

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 965273-(Pyrrol-1-yl)propiononitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130908821-(2-cyanoethyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1H-pyrrole-2-sulfonamideYield 16.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 2.59 g (0.021 mole) of 2-amino-4,6-dimethylpyrimidine in 80 ml dry tetrahydrofuran at -70° C. under nitrogen was added dropwise via syringe 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature of the reaction mixture below -55° C. The resulting solution was stirred 0.5 hour at -70°, then treated dropwise with a solution of 2.4 ml (0.021 mol) of N-(2-cyanoethyl)pyrole in 10 ml dry THF. A catalytic amount (approximately 0.2 to 0.3 gm) of aluminum (III) chloride was added and the reaction mixture allowed to warm to ambient temperatures and stirred for an additional 18 hours. The reaction mixture was poured into 300 ml of H2O and extracted with three portions of dichloromethane. The organic solutions were washed with water, dried over MgSO4 and evaporated. Trituration with a small volume of CH2Cl2 afforded 1.2 g of the desired product as a white microcrystalline solid, m.p. 158°-159° C. The infrared spectrum of the product included absorptions at 3250 and 3110 (NH), 2240 (C≡N), 1685 (C=O), 1350 and 1160 cm-1 (SO2).

Workup

  1. temperatureto maintain the temperature of the reaction mixture below -55° C
  2. temperatureto warm to ambient temperatures
  3. stirringstirred for an additional 18 hours
  4. extractionextracted with three portions of dichloromethane
  5. washThe organic solutions were washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-3d5973fec74e4e8d8684287ca326125b
Source dataset
uspto-grants-1984_09
Patent number
US04473394

Reaction notes

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