Pyrrolidine → HCID 22633028, compound

HRID 2270229Notes

Reaction equation

HRID 2270229 reaction equation
[CH2:1]([O:8][N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17]([F:21])[C:18](Cl)=[N:19][C:12]=2[N:11]([CH2:22][CH3:23])[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl>[CH2:1]([O:8][N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17]([F:21])[C:18]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[N:19][C:12]=2[N:11]([CH2:22][CH3:23])[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22632998HCID 22632998, compound

Product 1

HCID 22633028HCID 22633028, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-benzyloxy-7-chloro-1-ethyl-6-fluoro-1H-pyrido[2,3-d]-pyrimidine-2,4-dione (Example N-2, 146 mg, 0.42 mmol) in dichloromethane (3 mL) was added pyrrolidine (0.070 mL, 0.84 mmol) and the mixture was stirred at room temperature for 10 minutes. The reaction was diluted with dichloromethane (10 mL). The organic phase was washed with saturated aqueous sodium bicarbonate, dried on MgSO4, and concentrated. Washing the solid residue with hexane afforded 120 mg of the title compound as a solid, mp 189-190° C.

Workup

  1. washThe organic phase was washed with saturated aqueous sodium bicarbonate
  2. customdried on MgSO4
  3. concentrationconcentrated
  4. washWashing the solid residue with hexane

Sources & evidence

ORD record
ord-f7d36c44c67d407bb120af973f177244
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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