Pyridinium chloride → HCID 68554841, compound

HRID 2359883Notes

Reaction equation

HRID 2359883 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]1[NH2:16].Cl.N1C=CC=CC=1>O>[NH2:16][C:7]1[N:6]([CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]=2[OH:2])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 68550921HCID 68550921, compound

Product 1

HCID 68554841HCID 68554841, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

120 mg (0.45 mmol) 3-(2-methoxybenzyl)-3,4-dihydroquinazolin-2-amine and 5 g pyridine hydrochloride were combined and heated for 4 hours at approx. 140° C. After cooling the melt, the residue was dissolved in water, extracted three times with dichloromethane and the combined organic phases were dried, filtered and evaporated. The resulting crude product was purified over MPLC (silica gel: Bischoff Prontoprep 60-2540-C18E, 32 μm; mobile phase: CH3CN/H2O+0.1% acetic acid) and subsequent lyophilization yielded the target product as a beige white solid; 110 mg.

Workup

  1. temperatureAfter cooling the melt
  2. extractionextracted three times with dichloromethane
  3. customthe combined organic phases were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting crude product was purified over MPLC (silica gel: Bischoff Prontoprep 60-2540-C18E, 32 μm; mobile phase: CH3CN/H2O+0.1% acetic acid) and subsequent lyophilization

Sources & evidence

ORD record
ord-e27a5b14b6bc467db73f5f03f6a8c3b8
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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