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

HRID 32637Notes

Reaction equation

HRID 32637 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][N:12]([CH3:27])[C:13]=2[C:14]2[S:26][C:17]3[N:18]=[CH:19][N:20]=[C:21](S(C)(=O)=O)[C:16]=3[CH:15]=2)=[CH:5][CH:4]=1.CC1([N:35]2C(C3SC4N=CN=C(S(C)(=O)=O)C=4C=3)=CN=C2)C=CC=CC1.C(Cl)Cl.N>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][N:12]([CH3:27])[C:13]=2[C:14]2[S:26][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH2:35])[C:16]=3[CH:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 691941946-(1-Methylphenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidineHCID 691965576-[4-(4-Methoxyphenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylsulfonyl)thieno[2,3-d]pyrimidine2×

Product 1

HCID 691973206-[4-(4-Methoxyphenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by a similar process to that described for Example 8 but using 6-[4-(4-methoxyphenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylsulfonyl)thieno[2,3-d]pyrimidine (intermediate 106) in place of 6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine (Intermediate 17) followed by flash chromatography on silica eluting with DCM:MeOH (0-10%) then 1% NH3. Tan solid (0.91 g, 36%);

Sources & evidence

ORD record
ord-d1ad872ee19f4be7b93e814e225306c8
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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