2-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine → 2-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidine

HRID 1064306Notes

Reaction equation

HRID 1064306 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1>CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[NH:5][C:6]1[N:11]=[C:10]([C:12]2[NH:13][CH:14]=[N:15][CH:16]=2)[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

Product 1

HCID 222734742-(3-Chloroanilino)-4-(imidazol-5-yl)pyrimidineYield 75.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine (Method 2; 256 mg, 0.5 mmol) in MeOH (3 ml) and 2M hydrochloric acid (1 ml) was stirred for 15 minutes. The volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried and the solvent removed by evaporation. The residue was purified by column chromatography eluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7) to give the title compound 102 mg, (75%) as a solid. NMR: 6.95 (dd, 1H), 7.25-7.33 (m, 2H), 7.73 (dd, 1H), 7.81 (d, 2H), 8.06 (s, 1H), 8.46 (d, 1H), 9.68 (s, 1H), 12.48 (br s, 1H); m/z: 270.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with DCM and 7M methanolic ammonia solution (99.5:0.5 increasing in polarity to 93:7)

Sources & evidence

ORD record
ord-c4eda35d17aa414391e683ecee4a8562
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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