N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine → 6-[1-(3,4-Dimethoxybenzyl)-4-phenyl-1H-imidazol-5-yl]-4-(methylthio)thieno[2,3-d]pyrimidine

HRID 32524Notes

Reaction equation

HRID 32524 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:6][N:7]=[CH:8][C:9]1[S:19][C:12]2[N:13]=[CH:14][N:15]=[C:16]([S:17][CH3:18])[C:11]=2[CH:10]=1.CO[C:27]1[CH:28]=[C:29]([CH:42]=[CH:43][C:44]=1OC)[CH2:30][N:31]=[CH:32]C1SC2N=CN=CC=2C=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:6][N:7]1[C:8]([C:9]2[S:19][C:12]3[N:13]=[CH:14][N:15]=[C:16]([S:17][CH3:18])[C:11]=3[CH:10]=2)=[C:30]([C:29]2[CH:42]=[CH:43][CH:44]=[CH:27][CH:28]=2)[N:31]=[CH:32]1

Participants

3

Reactant 2

HCID 17965764N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine2×HCID 69195986N-(3,4-dimethoxybenzyl)-N-{[4-(methylthio)thieno[2,3-d]pyrimidin-6-yl]methylidene}amine2×

Product 1

HCID 179657606-[1-(3,4-Dimethoxybenzyl)-4-phenyl-1H-imidazol-5-yl]-4-(methylthio)thieno[2,3-d]pyrimidineYield 55%

Procedure

The title compound was prepared in 55% yield using a procedure similar to the one described for example 6 above but starting from N-(3,4-dimethoxybenzyl)-N-{[4-(methylthio)thieno[2,3-d]pyrimidin-6-yl]methylidene}amine (intermediate 18) (76 mg), in place of N-(3,4-dimethoxybenzyl)-N-[thieno[2,3d]pyrimidin-6-ylmethylidene]amine (intermediate 14);

Sources & evidence

ORD record
ord-8db58ff812ce41e083de97f866f31b2c
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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