3-Amino-1-propanol → HCID 135433506, compound

HRID 363364Notes

Reaction equation

HRID 363364 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.[NH2:19][CH2:20][CH2:21][CH2:22][OH:23]>C(O)CC>[OH:23][CH2:22][CH2:21][CH2:20][NH:19][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 90863-Amino-1-propanolHCID 178458304HCID 178458304, compound

Product 1

HCID 135433506HCID 135433506, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A stirred solution of 4-chloro-6-hydroxy-2-(2-propoxyphenyl)pyrimidine (0.66 g) and 3-amino-1-propanol (0.56 g) in n-propanol was heated under reflux for 16 hours. The cooled reaction mixture was evaporated under reduced pressure to yield an oil which was partitioned between chloroform (20 ml) and water (20 ml). The chloroform layer was separated from the aqueous layer which was extracted with chloroform (2×10 ml) and the combined chloroform layers were washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from isopropanol:diethyl ether to yield the title compound, 0.54 g, m.p. 147.5°-148.5° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe cooled reaction mixture
  3. customwas evaporated under reduced pressure
  4. customto yield an oil which
  5. customwas partitioned between chloroform (20 ml) and water (20 ml)
  6. customThe chloroform layer was separated from the aqueous layer which
  7. extractionwas extracted with chloroform (2×10 ml)
  8. washthe combined chloroform layers were washed with water
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated under reduced pressure
  11. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-01a017a6fdcc498cab036fb016f8a4dd
Source dataset
uspto-grants-1999_02
Patent number
US05874440

Reaction notes

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