Tetrahydrofuran → HCID 135430303, compound

HRID 2258431Notes

Reaction equation

C(N(CC)CC)C.N1C=CC(CN)=CC=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([NH:30][CH2:31][CH3:32])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[O:33]1CCCC1>>[CH2:31]([NH:30][C:23]1[CH:22]=[C:21]2[C:26]([C:17](=[O:33])[NH:18][CH:19]=[N:20]2)=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28])[CH3:32]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 773174-Pyridinemethanamine

HCID 232929894-Chloro-7-ethylamino-6-nitroquinazoline

Product 1

HCID 135430303HCID 135430303, compound

Procedure

Triethylamine (10 ml, 72.1 mmol) and 4-picolylamine (4 ml, 39.4 mmol) were added to a tetrahydrofuran solution (20 ml) of 4-chloro-7-ethylamino-6-nitroquinazoline obtained from 7-ethylamino-6-nitro-4(3H)-quinazolone (737.9 mg, 3.15 mmol) according to the procedures in Reference Example 13 under ice-cooling. The mixture was stirred at room temperature for 13 hours and at 55° C. for 4 hours. After a solvent was distilled off, the residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=9:1) to give the title compound (780 mg, 76%).

Sources & evidence

ORD record: ord-9429503de19d43af8c5e9adcc0cbd4a8
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661147

Reaction notes

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