Diisopropylamine → HCID 178503449, compound

HRID 1369408Notes

Reaction equation

HRID 1369408 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

nBuLi (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 mm 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 mm 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-b78919cabc5d45dc80ee2862df945bac
Source dataset
uspto-grants-2003_06
Patent number
US06579874B2

Reaction notes

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