Triethylamine → 5-bromo-3-(2-chlorobenzyl)-2-(chloromethyl)quinazolin-4(3H)-one

HRID 632916Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12](=O)[CH2:13][Cl:14])[C:3]=1[C:4]([OH:6])=O.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].C(N(CC)CC)C.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:6])[N:20]([CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[Cl:16])[C:12]([CH2:13][Cl:14])=[N:11]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred mixture of compound (7a) (7.50 g, 27.4 mmol), 2-chlorobenzylamine (5.00 mL, 41.05 mmol) and triethylamine (5.70 mL, 41.1 mmol) in toluene (250 mL) was added a solution of phosphorus trichloride (2.60 mL, 30.1 mmol) in toluene (250 mL) dropwise over 1 hr. The reaction mixture was heated to 110° C. for 24 hr, whereupon the hot solution was decanted and concentrated in vacuo. The residue was triturated with propan-2-ol (50 mL) to afford the title compound (8) (6.41 g, 59%) as a yellow solid: m/z 397/399 (M+H)+ (ES+).

Workup

customwas decanted
concentrationconcentrated in vacuo
customThe residue was triturated with propan-2-ol (50 mL)

Sources & evidence

ORD record: ord-a4252ccd935b4dbd8265b34dc0da96e5
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321773B2

Reaction notes

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