Potassium Carbonate → HCID 68647620, compound

HRID 1984232Notes

Reaction equation

HRID 1984232 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.[CH3:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+]>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][CH2:28][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][N:22]3[CH3:21])[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 126443922-(Chloromethyl)-1-methylpiperidine--hydrogen chloride (1/1)HCID 686472384-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile

Product 1

HCID 68647620HCID 68647620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile (0.3 1 mmol), 1-methyl-2-chloromethyl-piperidine hydrochloride (0.41 mmol) and potassium carbonate (7.2 mmol) are stirred in DMF (3 ml) at 80° C. for 8 hours. The solvent is evaporated, the residue is dissolved in water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=9:1) as mobile phase. The product containing fractions are combined and evaporated. A pale oil with Rf=0.54 (CH2Cl2/MeOH=10:1) is obtained.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=9:1) as mobile phase
  7. additionThe product containing fractions
  8. customevaporated
  9. customA pale oil with Rf=0.54 (CH2Cl2/MeOH=10:1) is obtained

Sources & evidence

ORD record
ord-3acbb35580ab47beb852154d94103a65
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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