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

HRID 624566Notes

Reaction equation

HRID 624566 reaction equation
NCCN1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1.[NH2:23][CH2:24][C@H:25]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:26]([O:28][CH3:29])=[O:27].C(N(CC)CC)C>CO>[CH2:34]([O:33][C:31]([NH:30][CH:25]([CH2:24][N:23]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1)[C:26]([O:28][CH3:29])=[O:27])=[O:32])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110432213-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl esterHCID 867228796-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione2×

Product 1

HCID 86722890Methyl 2-(((benzyloxy)carbonyl)amino)-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 1

HCID 887MethanolSolvent

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate A Step 3) (1.342 g, 3.98 mmol), (S)-methyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate (1.207 g, 4.18 mmol) and triethylamine (1.665 ml, 11.94 mmol) were suspended in methanol (20 ml). The mixture was heated to reflux for 16 hours then cooled to room temperature and filtered. The residue was rinsed with methanol (20 ml) to afford the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. filtrationfiltered
  4. washThe residue was rinsed with methanol (20 ml)

Sources & evidence

ORD record
ord-9a6bb1eff1f84ae8a999ed56e5fbff66
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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