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

HRID 1453674Notes

Reaction equation

HRID 1453674 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][N:11]([CH3:26])[C:12]=2[C:13]2[S:25][C:16]3[N:17]=[CH:18][N:19]=[C:20](S(C)(=O)=O)[C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[NH3:27]>O1CCOCC1>[I:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][N:11]([CH3:26])[C:12]=2[C:13]2[S:25][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:27])[C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 690581946-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine

Product 1

HCID 103206356-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amineYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-[4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylsulfonyl)thieno[2,3-d]pyrimidine (200 mg) and concentrated aqueous ammonia (5 mL) was stirred in 1,4-dioxane (15 mL) for 17 hours. The solvent was evaporated and the residue purified by chromatography on silica eluting with a gradient of 0-50% EtOAc/DCM then 0-20% MeOH/DCM to give the title compound as a colourless solid (136 mg, 78%);

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography on silica eluting with a gradient of 0-50% EtOAc/DCM

Sources & evidence

ORD record
ord-486e83d7143a4a8abcdf34a7f18d8c38
Source dataset
uspto-grants-2009_01
Patent number
US07476677B2

Reaction notes

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