Phosphorus tribromide → 2-(2-(bromomethyl)phenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1624915Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22]O)[C:8]2=[O:24])=[CH:4][CH:3]=1.P(Br)(Br)[Br:28]>CC#N.O>[Br:28][CH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:9]1[C:8](=[O:24])[N:7]([CH2:6][C:5]2[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

According to Scheme 9 Step 1: To a stirred solution of 4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione (70 mg, 0.19 mmol) in CH3CN (10 mL) was added phosphorus tribromide (76 mg, 0.28 mmol) and the mixture was heated at 60° C. during two hours. The reaction mixture was diluted with 100 mL of water and the aqueous layer was extracted with DCM (×2). The combined organic layers were successively washed with water, with brine, dried over MgSO4, filtered and concentrated to afford 70 mg (Yield=86%) of 2-(2-(bromomethyl)phenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione. The product was pure enough to be used in the next step without any purification

Workup

extractionthe aqueous layer was extracted with DCM (×2)
washThe combined organic layers were successively washed with water, with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-28ece8979f0648f2be8380d8bfe4a04f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

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