Ammonia → HCID 69377277, compound

HRID 860758Notes

Reaction equation

HRID 860758 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])[C:5]([Cl:17])=[CH:4][N:3]=1.[S:18]([NH2:28])(=[O:27])([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)=[O:19].N>C(O)CCC>[S:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][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])[C:5]([Cl:17])=[CH:4][N:3]=2)=[CH:22][CH:21]=1)(=[O:19])(=[O:27])[NH2:28]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5333SulfanilamideHCID 79633195HCID 79633195, compound

Product 1

HCID 69377277HCID 69377277, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,5-Dichloro4-(2-cyanoanilino)pyrimidine (265 mg, 1.00 mmol) was dissolved in n-butanol (1 ml) and sulphanilamide (207 mg, 1.20 mmol) was added. The resulting suspension was heated at reflux for 2 hours and allowed to cool to ambient temperature. The reaction mixture was then basified using methanolic ammonia and evaporated onto silica. The residue was purified by column chromatography eluting with 0–15% 2.0M methanolic ammonia solution in dichloromethane to afford a solid product (42.6 mg). NMR (303.1K): 7.09 (2H, s), 7.41–7.59 (5H, m), 7.65 (1H, d), 7.74–7.86 (1H, m), 7.94 (1H, d 8.25 (1H, s), 9.46 (1H, s), 9.78 (1H, s); MS (M+H)+: 401, 403.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  3. customevaporated onto silica
  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-bdbabff9d6f54fc5922da287139fe3c0
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Reaction notes

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