2-Methyl-3-butyn-2-ol → HCID 19830644, compound

HRID 1493127Notes

Reaction equation

HRID 1493127 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=3[C:9](=[O:17])[N:8]([CH3:18])[CH2:7][C:6]=12.[CH3:19][C:20]([OH:24])([C:22]#[CH:23])[CH3:21]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:24][C:20]([CH3:21])([CH3:19])[C:22]#[C:23][C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=3[C:9](=[O:17])[N:8]([CH3:18])[CH2:7][C:6]=12

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 19830655HCID 19830655, compound

Product 1

HCID 19830644HCID 19830644, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

5 g (14.2 mmol) of 4,5-dihydro-3-iodo-5,7-dimethyl-6H -imidazo[1,5-a][1,4]benzodiazepin-6-one were heated to boiling under reflux for 4.5 hours with 1.50 g (17.8 mmol) of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenyl -phosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 40 ml of diethylamine. The reaction mixture was then evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. By recrystallization from ethyl acetate there was obtained 4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5,7-dimethyl -6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one of melting point 165-167°.

Workup

  1. customThe reaction mixture was then evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with ethyl acetate
  4. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e6a098294ccd41e8a140d0bead33eabd
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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