Water → 4-(2,2-Dimethyl-propylamino)-6-(pyridin-4-ylmethoxy)-quinazoline-2-carbonitrile

HRID 1163004Notes

Reaction equation

HRID 1163004 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1.Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 686472384-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile

Product 1

HCID 686473924-(2,2-Dimethyl-propylamino)-6-(pyridin-4-ylmethoxy)-quinazoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile (0.23 mmol), 4-chloromethyl-pyridine hydrochloride (0.35 mmol) and cesium carbonate (2.3 mmol) are stirred in DMF (3 ml) at RT for 20 hours. Water is added until a clear solution is formed. Then more water is added until the solution gets turbide. The precipitate formed is filtered off, washed with water and dried (vacuum). A powder with mp. 203-205° C., Rf=0.2 (CH2Cl2/MeOH=15:1) is obtained.

Workup

  1. customis formed
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried (vacuum)
  6. customA powder with mp. 203-205° C., Rf=0.2 (CH2Cl2/MeOH=15:1) is obtained

Sources & evidence

ORD record
ord-4793e1efeee6472b8e4c62b5f7a0631b
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

Loading…