Water → N-(3-Chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38524Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][N:20](C(OCC)=O)[CH2:21][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][NH:20][CH2:21][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 4-[(3-chloro-4-fluorophenyl)amino]-5,7-dihydro-6H-pyrrolo[3′,4′:4,5]thieno[2,3-d]pyrimidine-6-carboxylate from Example 22A (413 mg, 1.05 mmol) in ethanol (4 mL) was added a 10 M aqueous potassium hydroxide solution (2 mL), and the mixture was stirred for 14 h at 80° C. Subsequently, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water, dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with tert-butyl methyl ether, and the precipitate was collected by suction filtration to yield 126 mg (38%) of the title compound. The mother liquor was concentrated in vacuo and purified by preparative HPLC to yield further 35 mg (10%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed twice with water
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuo
customThe residue was triturated with tert-butyl methyl ether
filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record: ord-bcefb95473b8411b9f9717a3dd02c9ac
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

Loading…