Ammonia → HCID 9820527, compound

HRID 860756Notes

Reaction equation

HRID 860756 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])[CH:5]=[CH:4][N:3]=1.[S:17]([NH2:27])(=[O:26])([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[O:18].CO.N>C(O)CCC>[S:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]#[N:16])[CH:5]=[CH:4][N:3]=2)=[CH:21][CH:20]=1)(=[O:18])(=[O:26])[NH2:27]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 5333SulfanilamideHCID 17981137HCID 17981137, compound

Product 1

HCID 9820527HCID 9820527, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
95 °C

Procedure

2-Chloro-4-(2-cyanoanilino)pyrimidine (250 mg, 1.09 mmol) was dissolved in n-butanol (3 ml) and sulphanilamide (150 mg, 0.87 mmol) was added. The resulting suspension was treated with methanol until all the solid dissolved. The reaction mixture was heated at 95° C. for 12 hours and allowed to cool to ambient temperature. The reaction mixture was then basified to pH 9–10 using methanolic ammonia and evaporated onto silica (5 ml). The residue was purified by column chromatography eluting with 0–15% 2.0M methanolic ammonia solution in dichloromethane to afford a solid product (256 mg). NMR (303.1K): 6.58 (d, 1H), 7.24 (br s, 2H), 7.56 (m, 5H), 7.69 (d, 1H), 7.82 (t, 1H), 7.95 (d, 1H), 10.88 (br s, 1H), 11.07 (br s, 1H); MS (M+H)+: 367.1.

Workup

  1. dissolutiondissolved
  2. temperatureto cool to ambient temperature
  3. customevaporated onto silica (5 ml)
  4. customThe residue was purified by column chromatography
  5. washeluting with 0–15% 2.0M methanolic ammonia solution in dichloromethane

Sources & evidence

ORD record
ord-7adc0ad60d0d4dc1a618666503cb36f5
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Reaction notes

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