Benzyl isocyanate → N-{4-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}-N'-benzylurea

HRID 32642Notes

Reaction equation

HRID 32642 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH3:23])[C:12]=2[C:13]2[S:22][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:21])[C:15]=3[CH:14]=2)=[CH:4][CH:3]=1.NC1C=C(C2N=CN(C)C=2C2SC3N=CN=C(N)C=3C=2)C=CC=1.[CH2:47]([N:54]=[C:55]=[O:56])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[NH2:21][C:20]1[C:15]2[CH:14]=[C:13]([C:12]3[N:11]([CH3:23])[CH:10]=[N:9][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:55]([NH:54][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:56])=[CH:3][CH:4]=3)[S:22][C:16]=2[N:17]=[CH:18][N:19]=1

Participants

4

Reactant 3

HCID 76639Benzyl isocyanateHCID 690543996-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amineHCID 691971586-[4-(4-Aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine2×

Product 1

HCID 10027041N-{4-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}-N'-benzylurea

Procedure

The title compound was prepared by a similar process to that described for Example 186 but using 6-[4-(4-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Intermediate 112) in place of 6-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Intermediate 110) and using benzyl isocyanate in place of phenyl isocyanate. Yellow solid (10 mg, 36%);

Sources & evidence

ORD record
ord-a299d98bcb53471a9ae9b58c14d39210
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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