1-Butanol → Ethyl-2-[(2-amino-5,6,7,8-tetrahydroquinazoline-4-yl)amino]acetate

HRID 965649Notes

Reaction equation

HRID 965649 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.C(O)CCC.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27]>O>[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH:31][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)[CH3:27]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 15896202Ethyl-2-[(2-amino-5,6,7,8-tetrahydroquinazoline-4-yl)amino]acetateYield 72.1%

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 butanol (3 ml) was added glycine ethyl ester hydrochloride (152 mg, 1.10 mmol) at room temperature. After the mixture 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 silica gel chromatography (3% MeOH/CHCl3) to give the object compound (98.3 mg, 72.1%).

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 silica gel chromatography (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-198e15dbd6fe4ad19f271e7a55828dfe
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Reaction notes

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