Phosphorus oxybromide → HCID 22313258, compound

HRID 989721Notes

Reaction equation

HRID 989721 reaction equation
[NH2:1][C:2]1[N:11]=[C:10](O)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.P(Br)(Br)([Br:15])=O>C1(C)C=CC=CC=1>[Br:15][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=[C:2]([NH2:1])[N:11]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178508877HCID 178508877, compound

Product 1

HCID 22313258HCID 22313258, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 2-amino-5,6,7,8-tetrahydroquinazoline-4-ol (1.65 g, 10 mmol) in toluene (16.5 ml) was added phosphorous oxybromide (3 g) and the mixture was kept to warm in a bath (bath temperature 90-100° C.) for 2 hours. After confirming disappearance of the starting materials, the reaction mixture was poured into ice-water, and was extracted with chloroform and a saturated aqueous NaHCO3 solution. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3) to give the object compound (1.7 g, 75%).

Workup

  1. extractionwas extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (CHCl3)

Sources & evidence

ORD record
ord-f8df3f1650d642e8acce3d7790fe7ee9
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Reaction notes

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