5-Amino-4-fluoro-2-methylphenol → 4-Fluoro-2-methyl-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

HRID 38558Notes

Reaction equation

HRID 38558 reaction equation
[Cl:1][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.[NH2:22][C:23]1[C:24]([F:31])=[CH:25][C:26]([CH3:30])=[C:27]([OH:29])[CH:28]=1>>[ClH:1].[F:31][C:24]1[C:23]([NH:22][C:2]2[C:3]3[C:10]4[CH2:11][CH2:12][NH:13][CH2:14][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:28][C:27]([OH:29])=[C:26]([CH3:30])[CH:25]=1

Participants

3

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 49788563tert-Butyl 4-chloro-5,6-dihydropyrido(4',3':4,5)thieno(2,3-d)pyrimidine-7(8H)-carboxylate

Product 1

HCID 668500154-Fluoro-2-methyl-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

Procedure

The title compound was prepared in analogy to Example 65A from tert-butyl 4-chloro-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 11A (2.20 g, 6.75 mmol) and 5-amino-4-fluoro-2-methylphenol (1.00 g, 7.09 mmol) to yield 2.69 g (100%).

Workup

  1. customto yield 2.69 g (100%)

Sources & evidence

ORD record
ord-8930f1c9b8ac4a5a8467f94376ed84fd
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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