N-bromobutanimide → 3-benzyl-6-(benzyloxy)-5-bromopyrimidin-4(3H)-one

HRID 350891Notes

Reaction equation

HRID 350891 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([Br:23])=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 210890133-benzyl-6-(benzyloxy)-pyrimidin-4(3H)-one

Product 1

HCID 114060883-benzyl-6-(benzyloxy)-5-bromopyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-benzyl-6-(benzyloxy)-pyrimidin-4(3H)-one (from Step 1) (5.00 g, 17.1 mmol) and N-bromosuccinimide (3.15 g, 17.7 mmol) are strirred in 100 ml anhydrous dimethylformamide for 20 hours. The solution is poured onto 1 L of ice with stirring and allowed to come to room temperature, when the product is collected by filtration. (5.97 g). The product is recrystalized from 60 mL hot acetonitrile (4.75 g, 75%) 1H-NMR (400 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.28–7.44 (overlapping m, 9H), 7.24 (s, 1H), 5.43 (s, 2H), 5.12 (s, 2H). LC/MS tr=5.89 minutes (0–95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 254 nm, at 50° C.) ES-MS m/z 371 (M+H). HRMS m/z 371 (M+H) 371.0399, calc. 371.0395.

Workup

  1. customto come to room temperature
  2. filtrationwhen the product is collected by filtration
  3. customThe product is recrystalized from 60 mL hot acetonitrile (4.75 g, 75%) 1H-NMR (400 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.28–7.44 (overlapping m, 9H), 7.24 (s, 1H), 5.43 (s, 2H), 5.12 (s, 2H)
  4. customLC/MS tr=5.89 minutes (0–95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 254 nm, at 50° C.) ES-MS m/z 371 (M+H)

Sources & evidence

ORD record
ord-aa897b6f8b3e41f3ac0e03f7abc70c43
Source dataset
uspto-grants-2007_02
Patent number
US07183287B2

Reaction notes

Loading…