Cyclopropanecarboxaldehyde → HCID 136262648, compound

HRID 591592Notes

Reaction equation

HRID 591592 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:22][C:21](=[O:23])[C:20]4[C:15](=[CH:16][C:17]([O:26][CH3:27])=[CH:18][C:19]=4[O:24][CH3:25])[N:14]=3)=[CH:9][CH:8]=2)[CH2:3]1.[CH:28]1([CH:31]=O)[CH2:30][CH2:29]1.[H][H]>C(O)C.O=[Pt]=O>[CH:28]1([CH2:31][NH:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[NH:22][C:21](=[O:23])[C:20]5[C:15](=[CH:16][C:17]([O:26][CH3:27])=[CH:18][C:19]=5[O:24][CH3:25])[N:14]=4)=[CH:9][CH:8]=3)[CH2:3]2)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 136348024HCID 136348024, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136262648HCID 136262648, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-(4-(3-aminopyrrolidin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (14) (0.21 mmol) in ethanol (30 mL) was treated with PtO2 (0.050 g) followed by cyclopropanecarbaldehyde (0.100 mL). The reaction was stirred under 1 atmosphere of hydrogen for 24 hours, filtered through Celite, with ethanol washes, concentrated, and purified by flash chromatography on silica gel, eluting to afford the title compound 15.

Workup

  1. filtrationfiltered through Celite, with ethanol washes
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluting

Sources & evidence

ORD record
ord-d1cd3441f5f742d69bc3c8cb2ccca064
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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