HCID 13478333, compound → HCID 13478332, compound

HRID 371462Notes

Reaction equation

HRID 371462 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[C:4]=1[N:11]1[CH2:16][CH2:15][N:14](CC2C=CC=CC=2)[CH2:13][CH2:12]1)[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[C:4]=1[N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)[CH3:2]

Participants

5

Reactant 2

HCID 13478333HCID 13478333, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13478332HCID 13478332, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 33.5 g (0.107 mole) of 6-ethyl-5-[4-(phenylmethyl)-1-piperazinyl]-2,4-pyrimidinediamine in 400 ml of acetic acid was hydrogenated over 2 g of 20% palladium on charcoal under 3.5 atmospheres of hydrogen for 23 hours and filtered. The filtrate was concentrated in vacuo to dryness. The solid residue was poured into one liter of 2N sodium hydroxide solution. The solid was collected and washed with 500 ml of water. Recrystallization from acetonitrile and drying in vacuo at 59° C. for 16 hours gave 19.0 g of the product as a white solid; mp 204°-207° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. additionThe solid residue was poured into one liter of 2N sodium hydroxide solution
  4. customThe solid was collected
  5. washwashed with 500 ml of water
  6. customRecrystallization from acetonitrile
  7. customdrying in vacuo at 59° C. for 16 hours

Sources & evidence

ORD record
ord-ca9bd31c0c584b909c2d215ae22024c5
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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