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Water → 1-(3,4-Dimethoxyphenoxy)-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol

HRID 365179
Notes
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Reaction equation

HRID 365179 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[CH:2]1[O:4][CH2:3]1.[NH2:16][CH2:17][CH2:18][NH:19][C:20]1[N:21]([CH3:30])[C:22](=[O:29])[N:23]([CH3:28])[C:24](=[O:27])[C:25]=1[CH3:26].CN(C)C=O.O>C(Cl)Cl>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[O:5][CH2:1][CH:2]([OH:4])[CH2:3][NH:16][CH2:17][CH2:18][NH:19][C:20]1[N:21]([CH3:30])[C:22](=[O:29])[N:23]([CH3:28])[C:24](=[O:27])[C:25]=1[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 128188664-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dioneHCID 202378293,4-Dimethoxyphenyl glycidyl ether

Product 1

HCID 128188611-(3,4-Dimethoxyphenoxy)-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g. 3,4-Dimethoxyphenyl glycidyl ether and 8.5 g. 4-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dione in 5 ml. dimethylformamide are left to stand for 48 hours at ambient temperature. The reaction mixture is then dissolved in methylene chloride, shaken out five times with water and the organic phase is extracted with 1N acetic acid. The aqueous phase is rendered alkaline by the addition of dilute aqueous sodium hydroxide solution and then extracted with methylene chloride. After drying the extract, the solution is chromatographed over silica gel using, as elution agent, methylene chloride-methanol-ammoniacal methanol (saturated) (20:1:1 v/v/v). After evaporating the pure fractions, the residue obtained is recrystallized from ethyl acetate. There are obtained 2.0 g. (24% of theory) of the desired product in the form of colorless crystals; m.p. 103°-104° C.

Workup

  1. extractionthe organic phase is extracted with 1N acetic acid
  2. additionby the addition of dilute aqueous sodium hydroxide solution
  3. extractionextracted with methylene chloride
  4. customAfter drying the extract
  5. customthe solution is chromatographed over silica gel using, as elution agent, methylene chloride-methanol-ammoniacal methanol (saturated) (20:1:1 v/v/v)
  6. customAfter evaporating the pure fractions
  7. customthe residue obtained
  8. customis recrystallized from ethyl acetate
  9. customThere are obtained 2.0 g

Sources & evidence

ORD record
ord-29a35655462641bda172df2c5863c2cf
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04608383

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes