Ammonia → 6-(1-methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amine

HRID 32522Notes

Reaction equation

HRID 32522 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:19][C:10]3[N:11]=[CH:12][N:13]=[C:14](S(C)(=O)=O)[C:9]=3[CH:8]=2)=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=[CH:3]1.[NH3:26]>O1CCOCC1>[CH3:1][N:2]1[C:6]([C:7]2[S:19][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:26])[C:9]=3[CH:8]=2)=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 179657746-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine2×

Product 1

HCID 104704756-(1-methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amineYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine (intermediate 17) (30 mg) and concentrated NH3 (0.75 mL) were stirred in 1,4-dioxane (3 mL) for 1 hour. The solvent was evaporated and the resultant residue dissolved in a small volume of DCM. Isohexane was then added and the resultant solid filtered and dried in vacuo to give the title compound as a pale yellow solid (25 mg, 100%);

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resultant residue dissolved in a small volume of DCM
  3. additionIsohexane was then added
  4. filtrationthe resultant solid filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-587d6b1a503943c39e760b4f227d47a3
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

Loading…