5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one → HCID 178434445, compound

HRID 2241237Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:28]2[C:29](=[O:42])[N:30]([CH3:41])[C:31]([NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:32][CH:33]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](CC3C=CC(OC)=CC=3)[N:16]=[C:17]([CH3:18])[C:10]=12>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:28]2[C:29](=[O:42])[N:30]([CH3:41])[C:31]([NH:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[N:32][CH:33]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][N:16]=[C:17]([CH3:18])[C:10]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a 15 mL reaction tube was added 5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (16 mg, 0.028 mmol) and the solids were dissolved in trifluoroacetic acid (0.5 mL, excess). The solution was stirred in a sealed tube for 1 hour at 80° C. The solvent was removed and the crude material was purified by loading onto a 0.5 mm preparative TLC plate, eluting with 8% MeOH in ethyl acetate. The product was obtained as a pale orange semi-solid (1.9 mg, 15%). LRMS (APCI pos) m/e 443.3 (M+1). 1H NMR (400 MHz, CD3OD) 8.26 (d, J=5.5 Hz, 1H), 7.94 (br s, 1H), 7.73 (m, 1H), 7.54 (br d, 1H), 7.48 (br d, 1H), 7.39 (m, J=7.4 Hz, 6H), 7.23 (t, J=7.4 Hz, 1H), 6.31 (d, J=5.5 Hz, 1H), 3.66 (s, 3H), 2.72 (s, 3H).

Workup

customTo a 15 mL reaction tube
customThe solvent was removed
customthe crude material was purified
washeluting with 8% MeOH in ethyl acetate

Sources & evidence

ORD record: ord-c2df5880b8d14c55b0d879b1c5f2bd3f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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