Dimethylformamide → HCID 15896208, compound

HRID 965654Notes

Reaction equation

HRID 965654 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.Cl.[CH2:26]([O:28][C:29](=[O:33])[CH:30]([NH2:32])[CH3:31])[CH3:27]>O>[NH2:12][C:4]1[N:3]=[C:2]([NH:32][CH:30]([CH3:31])[C:29]([O:28][CH2:26][CH3:27])=[O:33])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 102560Alanine, ethyl ester, hydrochloride (1:1)HCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 15896208HCID 15896208, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °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 (4 ml) was added 2-aminopropionic acid ethyl ester hydrochloride (167 mg, 1.09 mmol) at room temperature. After the mixture was stirred for 2.5 hours at 100° 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 (5% MeOH/CHCl3) to give the object compound (42.1 mg, 29.3%).

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 (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-c4037760ea8e4254b81393c26b6dd8ba
Source dataset
uspto-grants-2005_10
Patent number
US06951866B2

Reaction notes

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