Dimethylformamide → N-(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)-N-(2-ethoxyethyl)amine

HRID 989695Notes

Reaction equation

HRID 989695 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.C(N(CC)CC)C.CN(C)C=O.[CH2:25]([O:27][CH2:28][CH2:29][NH2:30])[CH3:26]>O>[NH2:12][C:4]1[N:3]=[C:2]([NH:30][CH2:29][CH2:28][O:27][CH2:25][CH3:26])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66970EthoxyethylamineHCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 15896205N-(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)-N-(2-ethoxyethyl)amineYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-chloro-5,6,7,8-tetrahydroquinazoline-2-ylamine (100 mg, 0.545 mmol), triethylamine (221 mg, 2.18 mmol) and dimethylformamide (2 ml) was added ethoxyethylamine (98 mg, 1.10 mmol) at room temperature. After the mixture was stirred for 2.5 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 preparative TLC (10% MeOH/CHCl3) to give the object compound (41.7 mg, 32.4%).

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 preparative TLC (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-bbd38e7f81c640ae9b8e3161a9c12994
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Reaction notes

Loading…