1-(2-Pyrimidinyl)piperazine → HCID 68389139, compound

HRID 927307Notes

Reaction equation

HRID 927307 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](O)=[O:21])[CH:15]=1)[C:7]2=[O:23].CC1C=CC=C2C=1NC(=O)NC2=O.BrCC1C=C(C=CC=1)C(OC)=O.[N:49]1([C:55]2[N:60]=[CH:59][CH:58]=[CH:57][N:56]=2)[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:52]3[CH2:53][CH2:54][N:49]([C:55]4[N:56]=[CH:57][CH:58]=[CH:59][N:60]=4)[CH2:50][CH2:51]3)=[O:21])[CH:15]=1)[C:7]2=[O:23]

Participants

5

Reactant 4

HCID 887471-(2-Pyrimidinyl)piperazineHCID 3340238-METHYLQUINAZOLINE-2,4(1H,3H)-DIONEHCID 517981Methyl 3-(bromomethyl)benzoateHCID 86708863HCID 86708863, compound

Product 1

HCID 68389139HCID 68389139, compound

Procedure

The compound was prepared from 8-methyl-3-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dione (prepared from 8-methylquinazoline-2,4(1H,3H)-dione and methyl 3-(bromomethyl)benzoate using a procedure similar to those used for Examples 222 and 223), and 2-(piperazin-1-yl)pyrimidine using a procedure similar to those described for the synthesis of compound of Example 3. 1H NMR (DMSO-d6): 10.81 (s, 1H), 8.36 (d, J=4.5 Hz, 2H), 7.83 (d, J=7.5 Hz, 1H), 7.52 (d, J=7.2 Hz, 1H), 7.45-7.30 (m, 4H), 7.13 (t, J=7.7 Hz, 1H), 6.67 (t, J=4.7 Hz, 1H), 5.15 (s, 2H), 3.92-3.46 (m, 8H), 2.36 (s, 3H). MS: m/z 457.3 [M+H]+.

Sources & evidence

ORD record
ord-48f14627a9984d858e7acd31c529a293
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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