Ammonia → 4-[4-Chloro-2-((S)-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide

HRID 240623Notes

Reaction equation

CO[C:3]([C:5]1[S:34][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[O:21][C@H:22]3[CH2:27][CH2:26][CH2:25][N:24](C(=O)C(F)(F)F)[CH2:23]3)[C:7]=2[C:6]=1[CH3:35])=[O:4].[NH3:36]>CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[C:7]3[C:6]([CH3:35])=[C:5]([C:3]([NH2:36])=[O:4])[S:34][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:15]([O:21][C@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-{4-Chloro-2-[(S)-1-(2,2,2-trifluoro-acetyl)-piperidin-3-yloxy]-phenylamino}-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (150 mg) and ammonia in methanol (7M; 5 ml) were combined and heated at 100° C. in sealed tube. The reaction heated under these conditions for 48 h. The residue was purified by chromatography tho give the inteded product.

Workup

temperatureThe reaction heated under these conditions for 48 h
customThe residue was purified by chromatography
customtho give the inteded product

Sources & evidence

ORD record: ord-345aec5582ec4f23bfbb98a83d6ad2ef
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648068B2

Reaction notes

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