Tributylamine → 3-(2-Methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl ester

HRID 889206Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[CH2:12]([O:19][C:20](=[O:23])[CH:21]=[CH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:12]([O:19][C:20](=[O:23])[CH:21]=[CH:22][C:2]1[CH:3]=[N:4][C:5]([C:8](=[O:9])[NH:10][CH3:11])=[N:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 5-bromo-N-methylpyrimidine-2-carboxamide (0.14 g, 0.64 mmol) in DMF (5 mL) was added acrylic acid benzyl ester (0.13 g, 0.78 mmol), Pd(OAc)2 (14.3 mg), tri-o-tolyl phosphine (49 mg, 0.16 mmol), tributyl amine (0.48 g, 2.59 mmol). The reaction mixture was heated in microwave oven at 110° C. for 1 h. The reaction mixture was cooled to room temperature, partitioned in water (50 mL) and ethyl acetate (50 mL). Ethyl acetate layer was separated, dried (MgSO4), concentrated to give 3-(2-methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl ester as a solid, this was washed with hexanes and dried to give the 0.122 g of the product. LCMS (APCI) 298 (M+)

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned in water (50 mL)
customEthyl acetate layer was separated
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9abad802e6fa4c629df8d3603c22b2de
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252793B2

Reaction notes

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