Butylamine → N-(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)-N-butylamine

HRID 965653Notes

Reaction equation

HRID 965653 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([NH2:12])[N:3]=1.[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16]>O>[NH2:12][C:4]1[N:3]=[C:2]([NH:17][CH2:13][CH2:14][CH2:15][CH3:16])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 15896206N-(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)-N-butylamineYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloro-5,6,7,8-tetrahydroquinazoline-2-ylamine (100 mg, 0.545 mmol) and butylamine (2 ml) was stirred for 4 hours at 90° C. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered and the solvent in the filtrate was removed in vacuo. The residue was purified by column chromatography (10% MeOH/CHCl3) to give the object compound (94.5 mg, 78.9%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent in the filtrate was removed in vacuo
  6. customThe residue was purified by column chromatography (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-6f77872686a0467797171f74f000879e
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Reaction notes

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