Sodium Bicarbonate → 2-{4-[(Naphthalen-2-yl)methyl]piperazin-1-yl}pyrimidin-5-ol

HRID 1288567Notes

Reaction equation

HRID 1288567 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Cl[C:19]1[N:24]=[CH:23][C:22]([OH:25])=[CH:21][N:20]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:13][CH2:14][N:15]([C:19]2[N:24]=[CH:23][C:22]([OH:25])=[CH:21][N:20]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 9105371-(Naphthalen-2-ylmethyl)piperazineHCID 145957002-Chloro-5-pyrimidinol

Product 1

HCID 215029112-{4-[(Naphthalen-2-yl)methyl]piperazin-1-yl}pyrimidin-5-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4.50 g. of 1-(β-napthylmethyl)piperazine(as prepared in Example 7), 2.5 g. of 2-chloro-5-hydroxypyrimidine in 30 ml. of dimethylformamide is added 2.0 g. of sodium bicarbonate and the mixture is refluxed for six hours. The mixture is cooled and filtered and the filtrate concentrated to a small volume in vacuo. The concentrate is diluted with 100 ml. of water and the insoluble material is washed with water and hexane to yield 1-(β-napthylmethyl)-4-(5-hydroxy-2-pyrimidinyl)piperazine.

Workup

  1. additionTo a mixture of 4.50 g
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to a small volume in vacuo
  5. additionThe concentrate is diluted with 100 ml
  6. washof water and the insoluble material is washed with water and hexane

Sources & evidence

ORD record
ord-bb1802a043204db3a429850a29a37f65
Source dataset
uspto-grants-1976_10
Patent number
US03988457

Reaction notes

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