4-chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine → 2-(cyclohexylmethyl)-5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one

HRID 2241309Notes

Reaction equation

[CH:1]1([CH2:7][C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=3)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[N:32]=[C:33]([I:34])[C:26]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[CH:1]1([CH2:7][C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:25]4[CH:30]=[CH:29][N:28]=[C:27]5[N:31]([CH2:35][C:36]6[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=6)[N:32]=[C:33]([I:34])[C:26]=45)=[C:18]([F:23])[CH:17]=3)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(cyclohexylmethyl)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one (0.026 g, 0.082 mmol), 4-chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (0.033 g, 0.083 mmol; prepared according to the procedure of Example 84, Step D), and DMAP (0.020 g, 0.165 mmol) in bromobenzene (1 mL) under N2 was stirred at 150° C. for 4 days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The desired product (0.048 g, 86%) was obtained as a pale yellow solid. LRMS (APCI pos) m/e 680 (M+1).

Workup

customprepared
concentrationThe reaction was concentrated in vacuo
customto remove as much bromobenzene as possible and
customthen purified directly by flash column chromatography
washeluting with 20:1 CH2Cl2/MeOH

Sources & evidence

ORD record: ord-373ffa1a6685422ca37de64f9f99eac8
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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