2,4-Diamino-5-(1-benzyl-4-piperidinyl)pyrimidine → HCID 22461017, compound

HRID 280695Notes

Reaction equation

HRID 280695 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]2[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11][CH2:10]2)=[CH:4][N:3]=1>C(O)C.C(O)(=O)C.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 224610192,4-Diamino-5-(1-benzyl-4-piperidinyl)pyrimidine

Product 1

HCID 22461017HCID 22461017, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 26 g of 2,4-diamino-5-(1-benzyl-4-piperidinyl)pyrimidine in 700 ml of ethanol and 20 ml of acetic acid was hydrogenated over 5 g of Pd/C 10% at room temperature and normal pressure up to the standstill of the hydrogen uptake, whereupon it was filtered off from catalyst. The filtrate was concentrated and the crystalline residue was dissolved in 100 ml of water. Chromatography on Dowex 1 (×10 200-400 mesh) (a cation exchange resin) gave 2,4-diamino-5-(4-piperidyl)-pyrimidine of melting point 230°-231° C. (dec.) (from water).

Workup

  1. filtrationnormal pressure up to the standstill of the hydrogen uptake, whereupon it was filtered off from catalyst
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe crystalline residue was dissolved in 100 ml of water

Sources & evidence

ORD record
ord-3660bfa2a3294c3399cae2a660958eb5
Source dataset
uspto-grants-1986_05
Patent number
US04590270

Reaction notes

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