Potassium Hydroxide → HCID 19081610, compound

HRID 963385Notes

Reaction equation

HRID 963385 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH2:24][C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)=[O:4].[OH-].[K+]>CO>[C:3]([CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH2:24][C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19081650HCID 19081650, compound

Product 1

HCID 19081610HCID 19081610, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

640 mg of 5-(3'-(2-methoxycarbonylethyl-amino)-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine (Example 4n)) are treated with 8 ml of a 1M solution of potassium hydroxide in methanol and stirred at room temperature for 10 hrs. Insoluble material is filtered off from the mixture and the filtrate is concentrated. The residue is chromatographed on MCl-Gel CHP20P (Mitsubishi Corporation) with water/acetonitrile 3:1. 180 mg (26%) of 5-(3'-(2-carboxyethyl-amino)-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a white yellowish solid. M.p. 136°-140° (decomposition).

Workup

  1. filtrationInsoluble material is filtered off from the mixture
  2. concentrationthe filtrate is concentrated
  3. customThe residue is chromatographed on MCl-Gel CHP20P (Mitsubishi Corporation) with water/acetonitrile 3:1

Sources & evidence

ORD record
ord-210b1dbc483d43cc9b257b6fb35082b5
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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