a-Tosyl-(4-methoxybenzyl) isocyanide → 6-[4-(4-methoxyphenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylthio)thieno[2,3-d]pyrimidine

HRID 32635Notes

Reaction equation

HRID 32635 reaction equation
CC1C=CC(S([CH:11]([N+:20]#[C-:21])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=O)=O)=CC=1.[CH3:22][S:23][C:24]1[C:25]2[CH:32]=[C:31]([CH:33]=[N:34][CH3:35])[S:30][C:26]=2[N:27]=[CH:28][N:29]=1.COC1C=C(C=CC=1OC)CN=CC1SC2N=CN=CC=2C=1>>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]2[N:20]=[CH:21][N:34]([CH3:35])[C:33]=2[C:31]2[S:30][C:26]3[N:27]=[CH:28][N:29]=[C:24]([S:23][CH3:22])[C:25]=3[CH:32]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 2771655a-Tosyl-(4-methoxybenzyl) isocyanide2×HCID 17965764N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amineHCID 69059019N-[4-(methylthio)thieno[2,3-d]pyrimidin-6-ylmethylidene]methanamine2×

Product 1

HCID 691962606-[4-(4-methoxyphenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylthio)thieno[2,3-d]pyrimidineYield 39%

Procedure

The title compound was prepared by a similar process to that described for Example 6 but using isocyano(4-methoxyphenyl)methyl 4-methylphenyl sulfone (Intermediate 104) in place of PhTosMIC and N-[4-(methylthio)thieno[2,3-d]pyrimidin-6-ylmethylidene]methanamine (intermediate 16) in place of N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine (intermediate 14) to afford the title compound as a solid (2.69 g, 39%);

Workup

  1. customThe title compound was prepared by a similar process to that

Sources & evidence

ORD record
ord-138a40e6d8fa41c1b30fad660d1c04df
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

Loading…