Water → HCID 16059404, compound

HRID 1989015Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:16]=[CH:17][C:18]4[C:24](=[O:25])[C:23]([C:26]#[N:27])=[CH:22][N:21]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:19]=4[N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-:34].[K+].O>C(O)(C)(C)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[N:16]=[CH:17][C:18]4[C:24](=[O:25])[C:23]([C:26]([NH2:27])=[O:34])=[CH:22][N:21]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:19]=4[N:20]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-5-oxo-8-phenyl-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonitrile (Example 13F, 9 mg) in 1 mL of t-butanol was added potassium hydroxide (ground, 5 mg). The mixture was stirred at 85° C. for 1 hour. After cooling to rt, water was added and the precipitates were extracted into EtOAc. The organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under vacuum to leave 2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-5-oxo-8-phenyl-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide as a yellow solid (7.2 mg, 79%). 1H NMR (300 MHz, CDCl3) δ (ppm): 10.64 (br, 1H), 10.30 (s, 1H), 9.17 (s, 1H), 7.71 (m, 3H), 7.53 (br, 1H), 7.43 (m, 2H), 6.94 (br, 2H), 6.35 (br, 2H), 5.06 (br, 1H), 3.12 (m, 4H), 2.59 (m, 4H), 2.37 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H25N7O2: 456.51 (M+H), Found: 456.6.

Workup

temperatureAfter cooling to rt
extractionthe precipitates were extracted into EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customThe solvent was evaporated under vacuum

Sources & evidence

ORD record: ord-4f0c4c20aae44b7d94301d84760c4f53
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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