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

HRID 2201194Notes

Reaction equation

HRID 2201194 reaction equation
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:22][O:23][C:24](=[O:28])[CH2:25][CH2:26][NH2:27].C(N(CC)CC)C>CCO.C(Cl)Cl>[CH3:17][N:13]1[C:14]2=[CH:15][N:27]([CH2:26][CH2:25][C:24]([O:23][CH3:22])=[O:28])[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]1=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×HCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 86723437Methyl 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (3 g, 8.90 mmol), beta alanine methyl ester hydrochloride (1.242 g, 8.90 mmol) and triethylamine (2.480 mL, 17.80 mmol) in EtOH (63.6 mL) was heated to 100° C. for 90 min using microwave radiation. The reaction mixture was diluted with of DCM (80 ml) and washed with water and 0.1M HCl. The organic portion was dried by passing through a phase separating cartridge and concentrated in vacuo to yield the title compound as a pale yellow oil.

Workup

  1. washwashed with water and 0.1M HCl
  2. customThe organic portion was dried
  3. customseparating cartridge
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-122111b1d5424f66878f6db3eae71f9c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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