Water → HCID 20266386, compound

HRID 1719715Notes

Reaction equation

HRID 1719715 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[N:23]1[CH2:28][CH2:27][CH:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]1.O>CS(C)=O.CCOCC>[CH3:30][C:29]1([CH:26]2[CH2:27][CH2:28][N:23]([C:14]3[C:13]4[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH3:9])[CH:12]=4)[N:17]=[CH:16][N:15]=3)[CH2:24][CH2:25]2)[CH2:2][O:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 20266422HCID 20266422, compound

Product 1

HCID 20266386HCID 20266386, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Trimethylsulphoxonium iodide (2.25 g) was added portionwise to a stirred suspension of sodium hydride (0.5 g of a 50% dispersion in oil) in dimethylsulphoxide (20 cm3) and the mixture was stirred for 1 hour after which time 6,7-dimethoxy-4-[4-(1-oxoethyl)piperid-1-yl]quinazoline (3.15 g) was added in DMSO (10 cm3). After 1 hour the mixture was poured into water (50 cm3), extracted with dichloromethane (3×50 cm3) and the dried extracts (MgSO4) were evaporated to give an oil which was chromatographed on silica (Merck 60.9385) eluting with chloroform to give a viscous oil. Trituration with ether gave 2-methyl-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]oxirane slightly contaminated with the starting ketone (2.0 g).

Workup

  1. extractionextracted with dichloromethane (3×50 cm3)
  2. customthe dried extracts (MgSO4) were evaporated
  3. customto give an oil which
  4. customwas chromatographed on silica (Merck 60.9385)
  5. washeluting with chloroform
  6. customto give a viscous oil

Sources & evidence

ORD record
ord-326f0fb839a849819f3733b0e44ae4ba
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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