1-Methyl-1H-imidazole-4-carbaldehyde → (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-(1-methyl-1H-imidazol-4-ylmethyl)-amine

HRID 391006Notes

Reaction equation

HRID 391006 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.[CH3:20][N:21]1[CH:25]=[C:24]([CH:26]=O)[N:23]=[CH:22]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:13])[CH2:26][C:24]3[N:23]=[CH:22][N:21]([CH3:20])[CH:25]=3)=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 5734191-Methyl-1H-imidazole-4-carbaldehydeHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 86623542(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-(1-methyl-1H-imidazol-4-ylmethyl)-amineYield 93%

Procedure

(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)methylamine was reacted with 1-methyl-1H-imidazole-4-carbaldehyde using standard reductive amination conditions. The resulting crude material was triturated with diethyl ether and methanol to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-(1-methyl-1H-imidazol-4-ylmethyl)-amine as a solid (93% yield).

Workup

  1. customThe resulting crude material was triturated with diethyl ether and methanol

Sources & evidence

ORD record
ord-994297beb6674f94a7ae06e578a6d515
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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