HCID 86620354, compound → HCID 67342066, compound

HRID 1669269Notes

Reaction equation

HRID 1669269 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5]>O1CCCC1>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[CH:7][C:6]([C:4](=[O:5])[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:11][N:10]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 86620354HCID 86620354, compound

Product 1

HCID 67342066HCID 67342066, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methoxy-methyl-amide (2.46 g, 7.936 mmol) is suspended in anhydrous tetrahydrofuran (40 mL), and cooled to 0° C. with stirring under nitrogen. N-hexyl magnesium bromide (8.0 mL, 2.0 M in diethyl ether, 16 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully neutralized with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 1-[2-(4-Trifluoromethyl-phenyl)-pyrimidin-5-yl]-heptan-1-one (1.47 g, 4.36 mmol) is obtained in pure form after flash column chromatography.

Workup

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-867d6bfab76843b69aa22482898527c4
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…