Diisopropylethylamine → HCID 66955360, compound

HRID 1399676Notes

Reaction equation

HRID 1399676 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[C:35]([O:42][CH3:43])[CH:34]=1.COCCOC.O>[Cl-].[Na+].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:32][C:33]1[CH:38]=[CH:37][C:36]([C:2]2[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[C:35]([O:42][CH3:43])[CH:34]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3858606(4-Chloro-2-methoxyphenyl)boronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955360HCID 66955360, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.239 g; 0.75 mmol), tetrakis(triphenylphosphine) palladium(0) (0.087 mg; 0.075 mmol), N,N-diisopropylethylamine (0.517 mL; 3 mmol) and 4-chloro-2-methoxyphenylboronic acid (0.210 g; 1.125 mmol) in a mixture DME-water (2 mL) was heated in a sealed tube for 2.5 h. The mixture was diluted with brine and extracted with ethyl acetate. The combined organics were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.190 g (60%) of the title compound as a colorless oil.

Workup

  1. temperaturewas heated in a sealed tube for 2.5 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

Sources & evidence

ORD record
ord-9078a88b5a8f4d87b3048e35e0861892
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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