Ammonia → 1-[(2-Amino-5,6,7,8-tetrahydroquinazoline-4-yl)amino]pentane-2-ol
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.Cl.[OH:14][CH:15]([CH2:18][CH2:19][CH3:20])[CH2:16][NH2:17].C(N(CC)CC)C.N>C(Cl)(Cl)Cl.CN(C=O)C>[NH2:12][C:4]1[N:3]=[C:2]([NH:17][CH2:16][CH:15]([OH:14])[CH2:18][CH2:19][CH3:20])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-chloro-5,6,7,8-tetrahydroquinazoline-2-ylamine (184 mg, 1 mmol), 2-hydroxypentylamine hydrochloride (140 mg, 1 mmol), triethylamine (202 mg, 2 mmol) and DMF (1 ml) was warmed for 5 hours in a bath (bath temperature, 90° C.). The solvent in the filtrate was removed in vacuo and the residue was purified by silica gel column chromatography (CHCl3:MeOH:NH4OHaq=100:10:0.4) to give the crude product (210 mg). To the crude product was aqueous ammonia solution (5 ml) and chloroform (30 ml) and it was extracted. The organic layer was washed with saturated brine (20 ml), dried over sodium sulfate, filtered and the solvent in the filtrate was removed in vacuo to give the object compound (128 mg, 51%).
Workup
- customThe solvent in the filtrate was removed in vacuo
- customthe residue was purified by silica gel column chromatography (CHCl3:MeOH:NH4OHaq=100:10:0.4)
- customto give the crude product (210 mg)
- extractionwas extracted
- washThe organic layer was washed with saturated brine (20 ml)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent in the filtrate was removed in vacuo
Sources & evidence
- ORD record
- ord-8494891d541c4bdbbcfc177c32bc6692
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458798B1
Reaction notes
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