Diisopropylamine → HCID 178503449, compound

HRID 396362Notes

Reaction equation

HRID 396362 reaction equation
[Li][CH2:2][CH2:3][CH2:4]C.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1.[F:22]C1C=CC(C(N(OC)C)=O)=CC=1.[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1>CCCCCC>[F:22][C:14]1([CH2:13][C:37]([C:36]2[CH:35]=[CH:39][CH:4]=[CH:3][CH:2]=2)=[O:38])[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[NH:15]1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineHCID 140693474-Fluoro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 178503449HCID 178503449, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

n-BuLi (10 ml of a 1.6 M solution in hexane; 12 mmol) is added at −78° C. to a solution of diisopropylamine (2.48 ml; 17 mmol) in THF (15 ml) and stirred for 5 min. 4-Methyl-2-(methylthio)pyrimidine (2 g; 14.5 mmol) dissolved in THF (2 ml) is added dropwise and stirred for 30 min at −78 C. 4-Fluoro-N-methoxy-N-methylbenzamide (2.66 g; 14.5 mmol) is dissolved in THF (3 ml) and added slowly to the reaction mixture. The mixture is warmed to r.t. within 45 min. and poured on water and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4 and evaporated to dryness to yield 2.5 g (65%) of yellow crystals after recrystallisation from tert.butyl methyl ether/hexane.

Workup

  1. additionis added dropwise
  2. stirringstirred for 30 min at −78 C
  3. additionadded slowly to the reaction mixture
  4. additionpoured on water
  5. extractionextracted with ethyl acetate three times
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-88b971d610324d35b96afbbfa5bc4890
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Reaction notes

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