Diisopropylethylamine → Methyl 2-(2-(2-chlorophenyl)-4-methyl-6-phenylpyrimidin-5-yl)pentanoate

HRID 1399573Notes

Reaction equation

HRID 1399573 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.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>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 27343222-Chlorophenylboronic acidHCID 86665646Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 50996971Methyl 2-(2-(2-chlorophenyl)-4-methyl-6-phenylpyrimidin-5-yl)pentanoateYield 66.1%

Reagents, catalysts & solvents 3

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

Procedure

Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (100 mg; 0.314 mmol), 2-chlorophenylboronic acid (73.6 mg; 0.471 mmol) and tetrakis(triphenylphosphine) palladium(0) (36.2 mg; 0.031 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (1.50 mL) and water (0.5 mL). N,N-Diisopropylethylamine (0.193 mL; 1.255 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 (2-20%) in heptane to give 82 mg (66%) of the title compound. ESI/APCI(+): 395 (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 (2-20%) in heptane

Sources & evidence

ORD record
ord-7b473e1f32144782baccf61761d51cd0
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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