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

HRID 32579Notes

Reaction equation

HRID 32579 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10]([CH:12]=[N:13][CH3:14])[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.COC1C=C(C=CC=1OC)CN=CC1SC2N=CN=CC=2C=1.CC1C=CC(S([CH:47]([C:50]2[CH:55]=[CH:54][C:53]([Br:56])=[CH:52][CH:51]=2)[N+:48]#[C-:49])(=O)=O)=CC=1>>[Br:56][C:53]1[CH:52]=[CH:51][C:50]([C:47]2[N:48]=[CH:49][N:13]([CH3:14])[C:12]=2[C:10]2[S:9][C:5]3[N:6]=[CH:7][N:8]=[C:3]([S:2][CH3:1])[C:4]=3[CH:11]=2)=[CH:55][CH:54]=1

Participants

4

Reactant 3

HCID 2771757a-Tosyl-(4-bromobenzyl) 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 691957936-[4-(4-bromophenyl)-1-methyl-1H-imidazol-5-yl]4-(methylthio)thieno[2,3-d]pyrimidine

Procedure

The title compound was prepared by a similar process to that described for Example 6 but using 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) and (4-bromophenyl)(isocyano)methyl 4-methylphenyl sulfone (Intermediate 66) in place of PhTosMIC. Pale yellow solid (1.7 g, 81%);

Sources & evidence

ORD record
ord-4a849c19de024884b51e535e926ab995
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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