Triethylamine → HCID 53257797, compound

HRID 2360576Notes

Reaction equation

HRID 2360576 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.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(CC)CC>CCO>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[N:5]=[C:4]([NH2:12])[N:3]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 137078204-Chloro-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 53257797HCID 53257797, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-5,6,7,8-tetrahydro-quinazolin-2-ylamine (100 mg, 0.55 mmol), N-methyl piperazine (91 uL, 1.5 mmol) and Et3N (140 uL, 1.1 mmol) in EtOH (2 ml) was heated at 70° C. for 16 h. The mixture was cooled to rt and concentrated, and the crude residue was purified (2 M NH3 in MeOH/CH2Cl2) to yield a white solid (31 mg, 23%). MS (ESI): mass calcd. for C13H21N5, 247.3; m/z found, 248.2 [M+H]+. 1H NMR (MeOD): 3.30-3.23 (m, 4H), 3.21 (dt, J=3.3, 1.6, 1H), 2.49 (t, J=6.7, 2H), 2.47-2.41 (m, 4H), 2.36 (t, J=5.9, 2H), 2.23 (s, 3H), 1.77-1.67 (m, 2H), 1.62-1.52 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customthe crude residue was purified (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c96da324659a42148b728dccaca7da88
Source dataset
uspto-grants-2014_04
Patent number
US08686142B2

Reaction notes

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