3-Amino-1-propanol → HCID 21647108, compound

HRID 892438Notes

Reaction equation

HRID 892438 reaction equation
Cl[C:2]1[CH:7]=[C:6](O)[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:6]1[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]=[CH:2][CH:7]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 178458304HCID 178458304, compound

Product 1

HCID 21647108HCID 21647108, 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 sulphate) and evaporated under reduced pressure. The residue was recrystallised 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 sulphate)
  10. customevaporated under reduced pressure
  11. customThe residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-0b0939623dfe42d2af79b61bf26c7674
Source dataset
uspto-grants-1992_06
Patent number
US05118686

Reaction notes

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