Phosphorus oxychloride → 4-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

HRID 965668Notes

Reaction equation

HRID 965668 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(Cl)(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl: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 24813Phosphorus oxychlorideHCID 178508877HCID 178508877, compound

Product 1

HCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amineYield 60.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-amino-5,6,7,8-tetrahydroquinazoline-4-ol (20.0 g, 121 mmol) in toluene (150 ml) was dropped phosphorus oxychloride (55.7 g, 363 mmol) at 90° C. The mixture was stirred for 1 hour and the solvent was removed in vacuo. The residue was poured into 28% aqueous ammonia solution at 0° C. The solid was filtered and purified by silica gel column chromatography (3% MeOH/CHCl3) to give the object compound (13.5 g, 60%).

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was poured into 28% aqueous ammonia solution at 0° C
  3. filtrationThe solid was filtered
  4. custompurified by silica gel column chromatography (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9b21a33dfa43433ab8fe68f324475bb1
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Reaction notes

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