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

HRID 1713193Notes

Reaction equation

HRID 1713193 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 stirred 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 recrystallized 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 recrystallized 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-b62a48db1a5143079f4159471b4b6461
Source dataset
uspto-grants-2010_09
Patent number
US07795271B2

Reaction notes

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