Sodium Carbonate → 6-{[6-(2-Fluoro-6-methoxyphenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester

HRID 1926956Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:31]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:31]3[C:32]([O:36][CH3:37])=[CH:33][CH:34]=[CH:35][C:30]=3[F:29])[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 150 mg (0.34 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 142 mg (0.84 mmol) (2-fluoro-6-methoxyphenyl)boronic acid in 2.0 ml 1,2-dimethoxyethane and add 0.34 ml of 2 M aqueous sodium carbonate solution and 24 mg (0.03 mmol) 1,1′-bis(diphenylphosphano)ferrocene palladium(II) chloride. Next, stir for 15 h at 80° C. Purify the reaction mixture directly by preparative RP-HPLC (gradient: water/acetonitrile). 56 mg (34% of theor.) of the desired product is obtained.

Workup

customPurify the reaction mixture directly by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record: ord-a51acfefdeff4b4eaecfd5580a395fee
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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