N-BOC-ethylenediamine → [2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 624588Notes

Reaction equation

HRID 624588 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.[NH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CCO>[C:27]([O:26][C:25](=[O:31])[NH:24][CH2:23][CH2:22][N:21]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:9]2[C:14]([N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]2=[O:20])=[CH:15]1)([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 86722910[2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione (step 3) (1 g, 2.97 mmol) in EtOH (12 mL) was treated with TEA (0.41 mL, 2.97 mmol) and tert-butyl 2-aminoethylcarbamate (commercial) (0.465 mL, 2.97 mmol). The mixture was heated to 100° C. for 1 h using microwave irradiation. After this time, a white precipitate had formed. The solid was collected via reduced pressure filtration and was washed with diethyl ether. The title compound was obtained as white needles.

Workup

  1. custommicrowave irradiation
  2. customAfter this time, a white precipitate had formed
  3. filtrationThe solid was collected via reduced pressure filtration
  4. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-3711a3eece1144e5bd871a3f47bca447
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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