Propargyl bromide → HCID 19066364, compound

HRID 1289225Notes

Reaction equation

HRID 1289225 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]2[C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][C:16]=3[CH2:15][CH2:14]2)[N:23]=[C:22]([CH3:26])[N:21]([CH2:27][O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:20]4=[O:35])[CH:9]=[CH:8][C:3]=1[CH:4]=[C:5]([CH3:7])[CH3:6].[CH2:36](Br)[C:37]#[CH:38].C(=O)([O-])[O-].[Ca+2]>CC(N(C)C)=O>[F:1][C:2]1[CH:11]=[C:10]([N:12]([CH:13]2[C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][C:16]=3[CH2:15][CH2:14]2)[N:23]=[C:22]([CH3:26])[N:21]([CH2:27][O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:20]4=[O:35])[CH2:38][C:37]#[CH:36])[CH:9]=[CH:8][C:3]=1[CH:4]=[C:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10112Calcium CarbonateHCID 19066319HCID 19066319, compound

Product 1

HCID 19066364HCID 19066364, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]-β,β-dimethylstyrene (1.4 g), propargyl bromide (6.1 g), calcium carbonate (0.88 g) and DMA (20 ml) was stirred and heated to 80° C. for 6 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using initially increasingly polar mixtures of hexane and ethyl acetate and then increasingly polar mixtures of methylene chloride and ethyl acetate as eluant. There was thus obtained o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]-β,β-dimethylstyrene (1.04 g);

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. temperatureincreasingly polar mixtures of methylene chloride and ethyl acetate as eluant

Sources & evidence

ORD record
ord-9fb105bed7754994ae171bd20a3b10b1
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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