Potassium Carbonate → HCID 136336917, compound

HRID 1723030Notes

Reaction equation

HRID 1723030 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][C:16]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:19][C:18](=[O:28])[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[OH2:1].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][C:16]3[N:21]=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:19][C:18](=[O:28])[CH:17]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 92467p-(1-Piperazinyl)phenolHCID 1355047536-(chloromethyl)-2-phenylpyrimidin-4-ol

Product 1

HCID 136336917HCID 136336917, compoundYield 131.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.46 g (25 mmol) of 1-(4-hydroxyphenyl)piperazine and 5.52 g (25 mmol) of 6-chloromethyl-2-phenyl-4-pyrimidone in 90 ml of absolute N,N-dimethylformamide (DMF) was warmed to 80° C., and 576 mg of powdered K2CO3 was added with stirring under a nitrogen atmosphere in each case after 10 minutes, after a further 25 minutes, and after a further 60 minutes (total addition of 1.73 g (12.5 mmol) of K2CO3), and the mixture was stirred for a further 3.5 hours at 80° C. The DMF was then substantially removed by distillation in vacuo in a rotary evaporator,170 ml of water and 17 ml of 4N HCl were added to the residue, and the resultant mixture was extracted three times with CH2Cl2. The CH2Cl2 extract was discarded. The acidic aqueous solution was treated with activated charcoal, shaken thoroughly, and filtered under suction. The filtrate was neutralized using 2N NaOH. The crystalline precipitate precipitating during this was filtered off under suction, washed with water, boiled for 5 minutes with methanol, and, after cooling to 10°-15° C., filtered off under suction and dried. 6.25 g (=69% yield) of pure 4-(4-hydroxyphenyl)-1-(2-phenyl-3,4-dihydropyrimidin-4-on-6-ylmethyl)piperazine hydrate, melting point 246°-48° C., were obtained, analysis: C21H24N4O3 (MW 380.45) calc. C 66.30, H 6.36, N 14.73; found C 65.9, H 6.1, N 14.5%.

Workup

  1. stirringthe mixture was stirred for a further 3.5 hours at 80° C
  2. customThe DMF was then substantially removed by distillation in vacuo in a rotary evaporator,170 ml of water and 17 ml of 4N HCl
  3. additionwere added to the residue
  4. extractionthe resultant mixture was extracted three times with CH2Cl2
  5. extractionThe CH2Cl2 extract
  6. additionThe acidic aqueous solution was treated with activated charcoal
  7. stirringshaken thoroughly
  8. filtrationfiltered under suction
  9. customThe crystalline precipitate precipitating during
  10. filtrationthis was filtered off under suction
  11. washwashed with water
  12. waitboiled for 5 minutes with methanol
  13. temperatureafter cooling to 10°-15° C.
  14. filtrationfiltered off under suction
  15. customdried

Sources & evidence

ORD record
ord-937995a9212a4fdcb6f9a47d40af97e6
Source dataset
uspto-grants-1989_08
Patent number
US04859670

Reaction notes

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