Hydrochloric Acid → Pyrido[2,3-d]pyrimidine, 4-[2-[4-(1,1-dimethylethyl)phenyl]ethoxy]-

HRID 2226836

Reaction equation

HRID 2226836 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].Cl>C1(C)C=CC=CC=1>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][O:24][C:2]2[C:3]3[CH:11]=[CH:10][CH:9]=[N:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79410p-tert-Butylphenethyl alcoholHCID 5690394-Chloropyrido[2,3-d]pyrimidine

Product 1

HCID 178230Pyrido[2,3-d]pyrimidine, 4-[2-[4-(1,1-dimethylethyl)phenyl]ethoxy]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 1.86 g (0.011 mole) of 4-chloropyrido-[2,3-d]pyrimidine, 2.0 g (0.011 mole) of 2-[4-(t-butyl)phenyl]ethanol, and 40 mL of toluene containing a little HCl gas was stirred at room temperature. The mixture was then cooled, and a yellow solid was collected. This was washed with hexane, then partitioned between 1N NaOH and CH2Cl2. The CH2Cl2 layer was dried over MgSO4, then the solvent was removed under vacuum to leave a yellow solid, which was recrystallized from hexane. Yield 2.5 g. M.P. 77°-79° C.

Workup

  1. temperatureThe mixture was then cooled
  2. customa yellow solid was collected
  3. washThis was washed with hexane
  4. custompartitioned between 1N NaOH and CH2Cl2
  5. dry with materialThe CH2Cl2 layer was dried over MgSO4
  6. customthe solvent was removed under vacuum
  7. customto leave a yellow solid, which
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-c2df3055639245a385a4bf028b77cccc
Source dataset
uspto-grants-1994_09
Patent number
US05350749

Linked notes

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