Water → HCID 22636924, compound

HRID 2416313Notes

Reaction equation

HRID 2416313 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]3([CH2:21][O:22][CH3:23])[CH2:20][CH2:19]3)[C:13]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[C:12]([O:31][CH2:32][CH3:33])[CH:11]=2)=[CH:4][N:3]=1.O>C(O)C.C(O)(=O)C.O=[Pt]=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:31][CH2:32][CH3:33])[C:13]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[C:14]([O:16][CH2:17][C:18]([CH3:19])([CH3:20])[CH2:21][O:22][CH3:23])[CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 69822884HCID 69822884, compound

Product 1

HCID 22636924HCID 22636924, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

4′-(2,4-Diamino-pyrimidin-5-ylmethyl)-2′-ethoxy-6′-(1-methoxymethyl-cydopropylmethoxy)-biphenyl-4-ol (235 mg; 0.52 mmol) is hydrogenated in ethanol/acetic acid conc./water (4/1/0.1) (10 ml) over PtO2 (6×35 mg) at 100° C. The reaction mixture is cooled to room temperature, the catalyst is filtered off with suction and the filtrate is concentrated. The residue is stirred in water, the pH is adjusted to pH 9 by addition of NH4OH conc., stirring is continued for 30 minutes and the mixture is filtered with suction. The grey crude product is then chromatographed over silica gel (20 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05). 104 mg (44%) 4′-(2,4-diamino-pyrimidin-5-ylmethyl)-6′-ethoxy-2′-(3-methoxy-2,2-dimethyl-propoxy)-biphenyl-4-ol are obtained as a colourless powder.

Workup

  1. customat 100° C
  2. filtrationthe catalyst is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. additionthe pH is adjusted to pH 9 by addition of NH4OH conc.
  5. stirringstirring
  6. filtrationthe mixture is filtered with suction
  7. customThe grey crude product is then chromatographed over silica gel (20 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05)

Sources & evidence

ORD record
ord-e8477956b5344c6e957c46ed42b34b30
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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