Allyl Alcohol → 2-Allyloxy-4-aminoquinazoline

HRID 354845

Reaction equation

HRID 354845 reaction equation
[Na].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](Cl)[N:4]=1.[CH2:14]([OH:17])[CH:15]=[CH2:16]>>[CH2:14]([O:17][C:5]1[N:4]=[C:3]([NH2:2])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH:15]=[CH2:16]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 2528792-Chloroquinazolin-4-amineHCID 5360545Sodium

Product 1

HCID 130604552-Allyloxy-4-aminoquinazoline

Conditions

Temperature
100 °C

Procedure

To the solution of sodium metal (0.7 g) in dried allylalcohol (90 ml) was added 4-amino-2-chloroquinazoline (3.5 g) and the mixture was stirred for 5 hours at 100° C. After the resultant mixture was concentrated under reduced pressure, to the residue was added a small volume of water. The aqueous mixture was extracted twice with ethyl acetate. The organic layer was washed with water and with aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crystalline residue, which was recrystallized from a mixture of ethyl acetate and hexane to give crystalline 2-allyloxy-4-aminoquinazoline (2.8 g).

Workup

  1. concentrationAfter the resultant mixture was concentrated under reduced pressure, to the residue
  2. additionwas added a small volume of water
  3. extractionThe aqueous mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with water and with aqueous solution saturated with sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a crystalline residue, which
  8. customwas recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-eb307d242d7a4c70a92a61bae7b04411
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Linked notes

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