Diisopropylethylamine → HCID 66956400, compound

HRID 1399745Notes

Reaction equation

HRID 1399745 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][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[N:24]1[C:33]2[C:28](=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=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]([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][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=[C:2]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:28]=2[CH:27]=[CH:26][CH:25]=[N:24]3)[N:7]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 5153389Quinolin-5-ylboronic acidHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 66956400HCID 66956400, compoundYield 65.8%

Reagents, catalysts & solvents 3

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

Procedure

Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.300 mmol), quinolin-5-ylboronic acid (156 mg; 0.901 mmol), tetrakis(triphenylphosphine) palladium(0) (34.7 mg; 0.030 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 (0.185 mL; 1.202 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 dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane to give 84 mg (43%) of the title compound as a colorless oil.

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 dichloromethane
  4. filtrationfiltered over a phase separator
  5. filtrationfilter (1PS)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane

Sources & evidence

ORD record
ord-d1d0ec9d963a434ea37db3f916cb5200
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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