Phenylboronic Acid → Methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetate

HRID 1399577Notes

Reaction equation

HRID 1399577 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:6]1[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]=1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 81531DiisopropylethylamineHCID 86665645Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)acetate

Product 1

HCID 66955384Methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetateYield 92.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)acetate (200 mg; 0.723 mmol), benzeneboronic acid (264 mg; 2.168 mmol), tetrakis(triphenylphosphine) palladium(0) (84 mg; 0.072 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (3 mL) and water (1 mL). N,N-Diisopropylethylamine (0.444 mL; 2.89 mmol) was added, the tube was sealed and irradiated in a microwave oven at 130° C. for 1 h. The reaction mixture was partitioned between brine and ethyl acetate, the phases were separated and the water layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane to give 212 mg (91%) of methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetate as a white solid. ESI/APCI(+): 319 (M+H).

Workup

  1. customthe tube was sealed
  2. customirradiated in a microwave oven at 130° C. for 1 h
  3. customThe reaction mixture was partitioned between brine and ethyl acetate
  4. customthe phases were separated
  5. extractionthe water layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane

Sources & evidence

ORD record
ord-42bd64f7225a4e37918f802b73120364
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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