Cesium carbonate → 4-Cyclopentylamino-6-[2-(4-methyl-piperazin-1-yl)-ethoxy]-quinazoline-2-carbonitrile

HRID 1984225Notes

Reaction equation

HRID 1984225 reaction equation
[CH:1]1([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[N:10]=[C:9]([C:18]#[N:19])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH:15]=3)[N:10]=[C:9]([C:18]#[N:19])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111839401-(2-Chloroethyl)-4-methylpiperazine dihydrochlorideHCID 686476604-Cyclopentylamino-6-hydroxy-quinazoline-2-carbonitrile

Product 1

HCID 686473854-Cyclopentylamino-6-[2-(4-methyl-piperazin-1-yl)-ethoxy]-quinazoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyclopentylamino-6-hydroxy-quinazoline-2-carbonitrile (0.4 mmol), 1-(2-Chloro-ethyl)-4-methyl-piperazine dihydrochloride (0.55 mmol) and cesium carbonate (4 mmol) are stirred in DMF (5 ml) at RT for 20 hours. The suspension is filtered, washed with little DMF and water is added to the filtrate until the solution gets turbide. The precipitate formed is filtered off, washed with water and dried (vacuum). A powder with mp. 110-112° C., Rf=0.48 (CH2Cl2/MeOH=9:2) is obtained.

Workup

  1. filtrationThe suspension is filtered
  2. washwashed with little DMF and water
  3. additionis added to the filtrate until the solution
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried (vacuum)
  8. customA powder with mp. 110-112° C., Rf=0.48 (CH2Cl2/MeOH=9:2) is obtained

Sources & evidence

ORD record
ord-118402fb13884095b3ce6c89cdf9146a
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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