Acetic Acid → HCID 22636904, compound

HRID 2416312Notes

Reaction equation

HRID 2416312 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:10][C:9]=2[O:26][CH2:27][C:28]2C=C[CH:31]=[CH:30][CH:29]=2)[CH:5]=[CH:6][CH:7]=1.[C:34](O)(=[O:36])[CH3:35]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:26][CH2:27][CH2:28][CH:29]3[CH2:30][CH2:31][O:36][CH2:34][CH2:35]3)=[CH:10][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:12][C:13]=2[O:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22636852HCID 22636852, compound

Product 1

HCID 22636904HCID 22636904, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(3′-Amino-2-benzyloxy-6-ethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (17.51 g; 39.7 mmol) is hydrogenated in ethanol (66 ml) and acetic acid conc. (198 ml) over Pd/C 10% (8.1 g) for 20 hours. The catalyst is filtered off and the mother liquor is concentrated. The residue is taken up in water and the pH is adjusted to 10 by addition of NH4OH conc. The suspension is filtered with suction and the crystals are washed thoroughly with water and dried under a high vacuum.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe mother liquor is concentrated
  3. additionthe pH is adjusted to 10 by addition of NH4OH conc. The suspension
  4. filtrationis filtered with suction
  5. washthe crystals are washed thoroughly with water
  6. customdried under a high vacuum

Sources & evidence

ORD record
ord-b8bbc9fbbdcb468f837bf7d7b1c58534
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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