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

HRID 1926954Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:23](Br)[O:22][C:18]=2[N:19]=[CH:20][N:21]=1.[F:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:23]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[F:35])[O:22][C:18]=2[N:19]=[CH:20][N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 0.22 ml of a 2 M aqueous sodium carbonate solution to a mixture of 100 mg (0.22 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 8 mg (0.01 mmol) bis(triphenylphosphine)palladium(II) chloride in 5.0 ml DMSO. Next, add 39 mg (0.28 mmol) (2-fluorophenyl)boronic acid and stir the mixture for 15 h at 80° C. Filter the reaction mixture and purify directly by preparative RP-HPLC (gradient: water/acetonitrile). 69 mg (29% of theor.) of the desired product is obtained.

Workup

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

Sources & evidence

ORD record: ord-893041709e314cf0bf7f2216fcd31761
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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