1-(Pyridin-2-ylmethyl)-1H-indazol-5-amine → N-[1-(Pyridin-2-ylmethyl)-1H-indazol-5-yl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]-pyrimidin-4-amine

HRID 38549Notes

Reaction equation

HRID 38549 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][N:29]1[C:37]2[C:32](=[CH:33][C:34]([NH2:38])=[CH:35][CH:36]=2)[CH:31]=[N:30]1>>[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][N:29]1[C:37]2[C:32](=[CH:33][C:34]([NH:38][C:2]3[C:3]4[C:10]5[CH2:11][CH2:12][NH:13][CH2:14][C:9]=5[S:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:35][CH:36]=2)[CH:31]=[N:30]1

Participants

3

Reactant 2

HCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amineHCID 49788563tert-Butyl 4-chloro-5,6-dihydropyrido(4',3':4,5)thieno(2,3-d)pyrimidine-7(8H)-carboxylate

Product 1

HCID 58116989N-[1-(Pyridin-2-ylmethyl)-1H-indazol-5-yl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]-pyrimidin-4-amine

Procedure

The title compound was synthesized in analogy to Example 12A from tert-butyl 4-chloro-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 11A (4.84 g, 14.5 mmol) and 1-(pyridin-2-ylmethyl)-1H-indazol-5-amine from Example 61A (3.50 g, 15.6 mmol) to yield 4.39 g (71%).

Workup

  1. customto yield 4.39 g (71%)

Sources & evidence

ORD record
ord-19577c89ba2a4755b76ed050067ed4ca
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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