5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → Ethyl 3-[1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl]-4-hydroxybenzoate

HRID 2175469Notes

Reaction equation

HRID 2175469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14]([C:22]1[C:23](=[O:33])[N:24]([CH3:32])[C:25](=[O:31])[N:26]([CH3:30])[C:27]=1[CH2:28]Br)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH3:30][N:26]1[C:27]2=[CH:28][N:1]([C:2]3[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=3[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:22]2[C:23](=[O:33])[N:24]([CH3:32])[C:25]1=[O:31]

Participants

4

Reactant 2

HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dioneHCID 12208891Ethyl 3-amino-4-hydroxybenzoate

Product 1

HCID 51361340Ethyl 3-[1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl]-4-hydroxybenzoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL round bottom flask ethyl 3-amino-4-hydroxybezoate (1.10 g, 6.07 mmol) and 4a (1.00 g, 2.98 mmol) were refluxed in ethanol (50 mL). After 2 h, the condenser was rearranged for distillation and ethanol (25 mL) was distilled off. The resulting solution was slowly poured into a vigorously stirred solution of ice cold water (200 mL) and citric acid (50 mg) giving a pink solid precipitate. The mixture was stirred for 10 min and then the solid was collected by filtration and rinsed with cold water to give 5h (1.23 g, 98.5%) after drying. The product was recrystallized from ethanol to give pale pink needles; m.p. 129.2-130° C. 1H NMR (600 MHz, CD2Cl2) δ 8.58 (s, 1H), 7.89 (dd, J=2.1, 8.7, 1H), 7.67 (d, J=2.1, 1H), 7.36-7.29 (m, 2H), 7.28-7.18 (m, 3H), 6.97 (d, J=8.7, 1H), 4.25 (q, J=7.1, 2H), 3.27 (s, 3H), 3.17 (s, 3H), 1.30 (t, J=7.1, 3H). 13C NMR (151 MHz, CD2Cl2) δ 165.40, 159.72, 156.82, 151.91, 136.06, 132.09, 130.86, 130.65, 129.49, 128.99, 128.83, 127.84, 125.70, 122.92, 117.65, 104.70, 103.11, 61.23, 32.02, 28.08, 14.24. MS (ES+) (m/z): [M+1]+ calculated for C23H22N3O5, 420.16. found 420.13.

Workup

  1. distillationthe condenser was rearranged for distillation and ethanol (25 mL)
  2. distillationwas distilled off
  3. additionThe resulting solution was slowly poured into a vigorously stirred solution of ice cold water (200 mL) and citric acid (50 mg)
  4. customgiving a pink solid precipitate
  5. filtrationthe solid was collected by filtration
  6. washrinsed with cold water

Sources & evidence

ORD record
ord-5c8de539e7d04374b2980b07f8964487
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

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