Triethylamine → N-(2-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)acetamide

HRID 1912355Notes

Reaction equation

HRID 1912355 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10].[C:12]([C:20]1[C:21](=[O:31])[N:22]([CH3:30])[C:23](=[O:29])[N:24]([CH3:28])[C:25]=1[CH2:26]Br)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(O)C>[CH3:28][N:24]1[C:25]2=[CH:26][N:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[NH:8][C:9](=[O:11])[CH3:10])[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:20]2[C:21](=[O:31])[N:22]([CH3:30])[C:23]1=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11149o-AminoacetanilideHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 68161872N-(2-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)acetamideYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of N-(2-aminophenyl)acetamide (315 mg, 2.1 mmol), bromo-compound 4 (680 mg, 2 mmol), triethylamine (200 mg, 280 μL, 2 mmol), and ethanol (2 mL) was microwave-heated at 170° C. for 1 h (2-5 mL vial, pressure 13 bar). The shiny white crystalline mass was filtered, washed, and recrystallized from ethanol to give 5 (392 mg, 51% yield): mp>250° C.; 1H NMR (DMSO-d6): δ 9.17 (s, 1H), 7.69 (d, 1H, pyrrole CH, J=8.06 Hz), 7.33-7.14 (m, 6H), 7.10-6.94 (m, 3H), 3.31 (s, 3H), 3.17 (s, 3H), 1.87 (s, 3H). MS (ES+) (m/z): [M+1]+ calculated for C22H21N4O3, 389.43. found 389.19.

Workup

  1. filtrationThe shiny white crystalline mass was filtered
  2. washwashed
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e795f693c0c348c6a7c1193af1983b6c
Source dataset
uspto-grants-2013_12
Patent number
US08609661B2

Reaction notes

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