Diisopropylamine → 1-(2,4-Dichlorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethan-1-one

HRID 639388Notes

Reaction equation

HRID 639388 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1.[Cl:22][C:23]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:24]=1[C:25](N(OC)C)=[O:26].[NH4+].[Cl-]>C(Cl)Cl.C1COCC1>[Cl:22][C:23]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:24]=1[C:25](=[O:26])[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineHCID 118453452,4-Dichloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 586416531-(2,4-Dichlorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 85 mL of diisopropylamine (Fluka 38300) and 2.5 L of THF at −75° C. under Argon is added 370 mL (0.55 Mol) of butyl lithium (BuLi; 1.6N in hexanes; Fluka 20160) within 1 h. To this is added 71 g (0.5 Mol) of 4-methyl-2-methylsulfanyl-pyrimidine in 250 mL of CH2Cl2 at −75° C. within 30 min. After this, a solution of 118 g (0.5 Mol) of 2,4dichloro-N-methoxy-N-methyl-benzamide in 250 mL of CH2Cl2 at −75° C. within 30 min followed by letting the mixture warn up to rt. After completion, the reaction mixture is poured onto 7 L of NH4Cl satd. and extracted with ethyl acetate. The combined organic layers are washed with brine, dried and evaporated. The crude product is suspended in hexanes. After filtering off and drying 1-(2,4-dichloro-phenyl)-2-(2-methylsulfanyl-pyrimidin-4-yl)-ethanone is obtained as yellow crystals. Title compound: m.p.: 105-107° C.; ES-MS: 313.0/314.9 [M+H]+.

Workup

  1. customwarn up to rt
  2. extractionand extracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. customdried
  5. customevaporated
  6. filtrationAfter filtering off
  7. dry with materialdrying 1-(2,4-dichloro-phenyl)-2-(2-methylsulfanyl-pyrimidin-4-yl)-ethanone
  8. customis obtained as yellow crystals

Sources & evidence

ORD record
ord-6ef35b94c319495d9161222c52b7dad9
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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