Dimethyl Sulfoxide → HCID 58016967, compound

HRID 1926929Notes

Reaction equation

COC(=O)[CH:4]([N:9]([C:11]1[C:12]2[C:19](Br)=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:13]=2[N:14]=[CH:15][N:16]=1)[CH3:10])[CH2:5][CH2:6][CH2:7][CH3:8].[C:28](=[O:31])([O-])[O-:29].[K+].[K+].[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.[CH3:45]S(C)=O>CO.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>[CH3:45][O:29][C:28](=[O:31])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:9]([C:11]1[C:12]2[C:19]([C:39]3[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=3)=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:13]=2[N:14]=[CH:15][N:16]=1)[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 200 mg (0.463 mmol) [(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)(methyl)amino]hexanoic acid methyl ester in 1.25 ml DMSO and 0.125 ml methanol. Add successively, under argon at RT, 16.2 mg (0.023 mmol) bis(triphenylphosphine)palladium(II) chloride, 127 mg (0.925 mmol) potassium carbonate and 105.4 mg (0.694 mmol) 4-methoxyphenylboronic acid. Heat the mixture to 80° C. for approx. 3 h, stirring vigorously. After cooling, purify the reaction mixture directly by preparative RP-HPLC (gradient: acetonitrile/water). 133.9 mg (63% of theor.) of the target product is obtained.

Workup

additionAdd successively, under argon at RT
temperatureAfter cooling
custompurify the reaction mixture directly by preparative RP-HPLC (gradient: acetonitrile/water)
custom133.9 mg (63% of theor.) of the target product is obtained

Sources & evidence

ORD record: ord-1a04fe3ccc024b38beec0d15f4bbb630
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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