HCID 12951525, compound → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(4-hydroxybenzyl)-4-pyrimidone

HRID 485657Notes

Reaction equation

HRID 485657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.[OH:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23](SC)=[N:24][CH:25]=2)=[CH:17][CH:16]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:23]2[NH:22][C:21](=[O:28])[C:20]([CH2:19][C:18]3[CH:29]=[CH:30][C:15]([OH:14])=[CH:16][CH:17]=3)=[CH:25][N:24]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 12951525HCID 12951525, compoundHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 202690732-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(4-hydroxybenzyl)-4-pyrimidoneYield 40.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.875 g) and 5-(4-hydroxybenzyl)-2-methylthio-4-pyrimidone (0.745 g) were refluxed in pyridine (3 ml) for 24 hours. The pyridine was evaporated in vacuo. Residual pyridine was removed from the residue by azeotroping with water in vacuo and dried by azeotroping with ethanol. Water (20 ml) was added and the pH lowered to 6 with dilute hydrochloric acid. The solid obtained was recrystallised from ethanol/water, dimethylformamide/water and finally acetic acid/water to give 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(4-hydroxybenzyl)-4-pyrimidone (0.54 g) m.p. 232°-4° C.

Workup

  1. customThe pyridine was evaporated in vacuo
  2. customResidual pyridine was removed from the residue
  3. customby azeotroping with water in vacuo
  4. customdried
  5. customby azeotroping with ethanol
  6. additionWater (20 ml) was added
  7. customThe solid obtained
  8. customwas recrystallised from ethanol/water, dimethylformamide/water and finally acetic acid/water

Sources & evidence

ORD record
ord-ca06fd15db644dbb97387d55c7943159
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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