Water → 4-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenol

HRID 32631Notes

Reaction equation

HRID 32631 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][N:18]([CH3:30])[C:19]=2[C:20]2[S:29][C:23]3[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=3[CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl.CO>[NH2:28][C:27]1[C:22]2[CH:21]=[C:20]([C:19]3[N:18]([CH3:30])[CH:17]=[N:16][C:15]=3[C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[S:29][C:23]=2[N:24]=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 17965779HCID 17965779, compound

Product 1

HCID 102456254-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenolYield 67.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-{4-[4-(Benzyloxy)phenyl]-1-methyl-1H-imidazol-5-yl}thieno[2,3-d]pyrimidin-4-amine (Example 53) (19 mg) was refluxed with TFA (3 mL) and water (0.05 mL) for 6 hr. The mixture was diluted with 1:1 DCM/MeOH and passed through an acidic extraction cartridge (Waters Oasis® MCX 1 g). The cartridge was washed with 1:1 DCM/MeOH, then eluted with concentrated aqueous NH3/DCM/MeOH 4:48:48. Fractions were evaporated to give the title compound as a solid (10 mg, 67%);

Workup

  1. washThe cartridge was washed with 1:1 DCM/MeOH
  2. washeluted with concentrated aqueous NH3/DCM/MeOH 4:48:48
  3. customFractions were evaporated

Sources & evidence

ORD record
ord-9b638fbee31848a89fe34d05bb1c4eeb
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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