Dimethylamine → 1-[2-(6-dimethylamino-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 445164Notes

Reaction equation

HRID 445164 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:39]=[CH:38][CH:37]=[CH:36][C:10]=1[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24]#[CH:25])=[CH:19][CH:20]=2)[C:15]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)=[N:14][C:13]1=[O:35].[CH3:40][NH:41][CH3:42]>>[CH3:40][N:41]([CH3:42])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:39]=[CH:38][CH:37]=[CH:36][C:10]=1[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24]#[CH:25])=[CH:19][CH:20]=2)[C:15]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)=[N:14][C:13]1=[O:35]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 601128261-[2-(6-Chloro-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Product 1

HCID 601128131-[2-(6-dimethylamino-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Conditions

Temperature
60 °C

Procedure

A mixture of 50 mg (92.1 μmol) 1-[2-(6-chloro-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one and 160 μl ethanolic dimethylamine solution (33%) is heated at 60° C. for 18 h. Extraction with dichloromethane and aqueous 0.1 M NaOH yields the title compound.

Workup

  1. extractionExtraction with dichloromethane and aqueous 0.1 M NaOH

Sources & evidence

ORD record
ord-d793865cff0b4c7283f36bde35d3a51e
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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