6-Bromomethyl-4-(3-methylanilino)quinazoline → HCID 22478403, compound

HRID 2184681Notes

Reaction equation

HRID 2184681 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.[Na].[SH:22][C:23]1[NH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1>>[N:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[NH:27][C:23]=1[S:22][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1

Participants

3

Reactant 2

HCID 224784026-Bromomethyl-4-(3-methylanilino)quinazolineHCID 178527776HCID 178527776, compound

Product 1

HCID 22478403HCID 22478403, compoundYield 59%

Procedure

Using an analogous procedure to that described in Example 34, 6-bromomethyl-4-(3-methylanilino)quinazoline was reacted with 2-mercaptobenzimidazole sodium salt to give 6-(2-benzimidazolylthiomethyl)4-(3-methylanilino)quinazoline in 59% yield, m.p. 123-129° C.; NMR Spectrum: 2.34 (s, 3H), 4.77 (s, 2H), 6.96 (d, 1H), 7.13 (m, 2H), 7.28 (t, 1H), 7.46 (broad s, 2H), 7.68 (m, 3H), 7.96 (m, 1H), 8.57 (s, 1H), 8.65 (d, 1H), 9.79 (broad s, 1H); Elemental Analysis: Found C, 64.9; H, 5.3; N, 15.9; C23H19N5S 1.6H2O 0.1CH3OH requires C, 64.5; H, 5.3; N, 16.3%.

Sources & evidence

ORD record
ord-24adbd1acf24492c97c10f73d75979fe
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

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