Binap, (A+-)- → [4-(2-Morpholin-4-yl-pyrimidin-4-ylamino)-naphthalen-1-yl]-oxo-acetic acid methyl ester

HRID 2353545Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:14][O:15][C:16](=[O:30])[C:17]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](Br)=[CH:21][CH:20]=1)=[O:18].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16](=[O:30])[C:17]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([NH:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:12]=2)=[CH:21][CH:20]=1)=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Morpholin-4-yl-pyrimidin-4-ylamine (140 mg, 0.77 mmol) and (4-bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester (18) (228 mg, 0.77 mmol) were suspended in 5 mL toluene and Pd(OAc)2 (5 mg, 3 mol %), BINAP (24 mg, 5 mol5) and CS2CO3 (753 mg, 2031 mmol) were added. The reaction mixture was stirred at 100° C. for 24hrs. The cooled mixture was purified by column chromatography (0-100% EtOAc/Hex) to yield 169 mg of target product.

Workup

customThe cooled mixture was purified by column chromatography (0-100% EtOAc/Hex)
customto yield 169 mg of target product

Sources & evidence

ORD record: ord-20e408c885394977afa5870433a9b291
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749999B2

Reaction notes

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