N,N-Dimethylaniline → 4-Chloro-6-nitro-2-(2-pyrazinyl)quinazoline

HRID 1520368Notes

Reaction equation

HRID 1520368 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)[NH:8][C:7]2=O)([O-:3])=[O:2].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:32]>>[Cl:32][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[C:9]([C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[N:8]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 136334003HCID 136334003, compound

Product 1

HCID 866770814-Chloro-6-nitro-2-(2-pyrazinyl)quinazoline

Conditions

Temperature
120 °C

Procedure

To a mixture of 6-nitro-2-(pyrazin-2-yl)quinazolin-4(3H)-one (1.00 g, 3.7 mmol) in POCl3 (10 mL) was added N,N-dimethylbenzenamine (0.1 mL). The resulting mixture was stirred at 120° C. for 2 h. After the reaction was completed, POCl3 was removed in vacuo, and the residue was co-evaporated with toluene twice to give a dark crude product, which was used for the next step without further purification.

Workup

  1. customPOCl3 was removed in vacuo

Sources & evidence

ORD record
ord-1b51e55b22424b0788fa26a38cb9ebba
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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