Ammonium Hydroxide → HCID 178426576, compound

HRID 1760975Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16](=[O:30])[C:17]3[CH:22]=[C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:20]=[C:19]([F:29])[CH:18]=3)[CH:12]=[CH:11][C:10]=2[CH3:31])[CH:5]=[CH:4][N:3]=1.[OH-:32].[NH4+]>C(O)=O>[F:29][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=1)[C:16]([NH:15][C:13]1[CH:12]=[CH:11][C:10]([CH3:31])=[C:9]([CH:14]=1)[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([OH:32])[N:7]=1)=[O:30]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-chloro-4-[5-(3-fluoro-5-morpholinobenzamido)-2-methylanilino]pyrimidine (0.1 g) and formic acid (1.0 ml) was stirred and heated to 65° C. for 16 hours. The mixture was allowed to cool to ambient temperature and was poured into a dilute aqueous ammonium hydroxide solution. The resultant precipitate was isolated and washed with anhydrous diethyl ether. There was thus obtained the title compound (0.09 g); NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 3.2 (m, 4H), 3.73 (m, 4H), 5.70 (br m, 1H), 6.95 (m, 1H), 7.09 (m, 1H), 7.19 (m, 1H), 7.25 (s, 1H), 7.4 (m, 1H), 7.5 (m, 1H), 7.68 (m, 1H), 10.14 (s, 1H), 10.5 (broad s, 1H); Mass Spectrum: M+H+ 424.

Workup

temperatureto cool to ambient temperature

Sources & evidence

ORD record: ord-1246e64094164c908252d3d1bf18599b
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846827B1

Reaction notes

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