Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate → 4-[2-((S)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-pyridin-3-ylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 240625Notes

Reaction equation

HRID 240625 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[C:18]([O:23][C@H:24]2[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]2)=[N:19][CH:20]=[CH:21][CH:22]=1>>[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:16][C:17]3[C:18]([O:23][C@H:24]4[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]4)=[N:19][CH:20]=[CH:21][CH:22]=3)[C:7]=2[C:6]=1[CH3:15])=[O:4]

Participants

3

Reactant 2

HCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 58413073(S)-tert-butyl 3-(3-aminopyridin-2-yloxy)piperidine-1-carboxylate2×

Product 1

HCID 584130704-[2-((S)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-pyridin-3-ylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Procedure

Prepared analogously to example 1.1. from 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester and (S)-tert-butyl 3-(3-aminopyridin-2-yloxy)piperidine-1-carboxylate (Intermediate X)

Workup

  1. customPrepared analogously to example 1.1

Sources & evidence

ORD record
ord-63ab46e01b204ad3b6e786949af8076f
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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