Hydrochloric Acid → HCID 22636833, compound

HRID 2416314Notes

Reaction equation

HRID 2416314 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][CH3:18])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][CH:20]=3)=[C:12]([O:29][CH2:30][C:31]3(/[CH:34]=[CH:35]/[C:36]#[N:37])[CH2:33][CH2:32]3)[CH:11]=2)=[CH:4][N:3]=1.Cl>CO>[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][CH3:18])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[C:12]([O:29][CH2:30][C:31]3(/[CH:34]=[CH:35]/[C:36]#[N:37])[CH2:32][CH2:33]3)[CH:11]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22636856HCID 22636856, compound

Product 1

HCID 22636833HCID 22636833, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(E)-3-[1-[4-(2,4-Diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methoxymethoxy-biphenyl-2-yloxymethyl]-cyclopropyl]-acrylonitrile (350 mg; 0.698 mmol) is stirred in methanol (12 ml) and a 3 M hydrochloric acid solution in methanol (3.4 ml) for 30 minutes at a bath temperature of 60° C. The methanol is evaporated off, the residue is dissolved in water (33 ml) and the pH is adjusted to approx. 9 by addition of NH4OH conc., whereupon the substance precipitates out. After stirring for 2 hours the mixture is filtered with suction and the residue is washed with water and dried under a high vacuum. 295 mg (92%) (E)-3-[1-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-hydroxy-biphenyl-2-yloxymethyl]-cyclopropyl]-acrylonitrile are obtained as a colourless powder.

Workup

  1. customThe methanol is evaporated off
  2. dissolutionthe residue is dissolved in water (33 ml)
  3. additionby addition of NH4OH conc.
  4. customwhereupon the substance precipitates out
  5. filtrationis filtered with suction
  6. washthe residue is washed with water
  7. customdried under a high vacuum

Sources & evidence

ORD record
ord-a4e3d4233a1e423097fd17d30f3f347d
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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