Water → 4-(2,2-Dimethyl-propylamino)-6-(pyridin-3-ylmethoxy)-quinazoline-2-carbonitrile

HRID 1984230Notes

Reaction equation

HRID 1984230 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:24]=[N:25][CH:26]=[CH:27][CH:28]=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:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 686472384-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile

Product 1

HCID 686474534-(2,2-Dimethyl-propylamino)-6-(pyridin-3-ylmethoxy)-quinazoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile (0.25 mmol), 3-chloromethyl-pyridine hydrochloride (0.38 mmol) and cesium carbonate (2.5 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. 156-158° C., Rf=0.35 (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. 156-158° C., Rf=0.35 (CH2Cl2/MeOH=15:1) is obtained

Sources & evidence

ORD record
ord-1dd0f91978d045258b36a5cbf3321be8
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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