7-ethoxy-N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine → 7-ethoxy-N4-(3-ethynylphenyl)quinazoline-4,6-diamine

HRID 1051120Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[CH:22])[CH:16]=3)=[N:9][CH:10]=[N:11]2)=[CH:6][C:5]=1[N+:23]([O-])=O)[CH3:2]>C(O)C.O.C(O)(=O)C.[Fe]>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[CH:22])[CH:16]=3)=[N:9][CH:10]=[N:11]2)=[CH:6][C:5]=1[NH2:23])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

7-ethoxy-N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine (8 g, 0.024 mol) was dissolved in a mixture of 80 ml ethanol, 80 ml H2O and 10 ml acetic acid. The reaction was heated to 70° C., then Fe (5.4 g, 0.096 mol) was added. The reaction mixture was heated to reflux for 4 hours. The resulting clear reaction solution was concentrated under reduced pressure to remove solvent. The pH of the residue was adjusted to 9 with 4N aqueous NaOH, and was washed with 200 ml EA/MeOH (50/1) until TLC show no product can be detected in the organic layer. The combined organic layers were concentrated, grey solid was precipitated and filtered to afford 7-ethoxy-N4-(3-ethynylphenyl)quinazoline-4,6-diamine as grey solid 5.4 g (74.2% yield).

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for 4 hours
concentrationThe resulting clear reaction solution was concentrated under reduced pressure
customto remove solvent
washwas washed with 200 ml EA/MeOH (50/1) until TLC
concentrationThe combined organic layers were concentrated
customgrey solid was precipitated
filtrationfiltered

Sources & evidence

ORD record: ord-b05bca8e799e4321a6fcf3f881d9b347
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388160B2

Reaction notes

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