Ethanolamine → HCID 135406932, compound

HRID 892437Notes

Reaction equation

HRID 892437 reaction equation
Cl[C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH3:18])[N:3]=1.[CH2:19]([CH2:21][NH2:22])[OH:20]>C(O)CCC>[OH:20][CH2:19][CH2:21][NH:22][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH3:18])[NH:5][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178458304HCID 178458304, compound

Product 1

HCID 135406932HCID 135406932, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred solution of 4-chloro-6-hydroxy-2-(2-propoxyphenyl)pyrimidine (0.43 g) and ethanolamine (0.3 g) in n-butanol (8 ml) was heated under reflux for 4 hours. The cooled reaction mixture was evaporated under reduced pressure to yield a residue which was washed with diethyl ether and then eluted from silica with chloroform: methanol (gradient elution). The combined fractions containing product were evaporated under reduced pressure to yield a crude product which was recrystallised from isopropanol:diethyl ether to yield the title compound, 0.28 g, m.p. 164.5°-65.5° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe cooled reaction mixture
  3. customwas evaporated under reduced pressure
  4. customto yield a residue which
  5. washwas washed with diethyl ether
  6. washeluted from silica with chloroform
  7. additionThe combined fractions containing product
  8. customwere evaporated under reduced pressure
  9. customto yield a crude product which
  10. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-001b7701532848c1b21671a8a9d8170b
Source dataset
uspto-grants-1992_06
Patent number
US05118686

Reaction notes

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