Water → Ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate

HRID 2200904Notes

Reaction equation

HRID 2200904 reaction equation
Cl.[CH:2]12[CH2:7][CH:6]1[CH2:5][NH:4][CH2:3]2.C(N(CC)CC)C.O.[F:16][C:17]1[CH:18]=[C:19]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:20][NH:21][C:22]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][N:25]=[C:24](S(C)=O)[N:23]=1>C(Cl)Cl>[CH:2]12[CH2:7][CH:6]1[CH2:5][N:4]([C:24]1[N:23]=[C:22]([NH:21][CH2:20][C:19]3[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:17]([F:16])[CH:18]=3)[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][N:25]=1)[CH2:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 223352893-Azabicyclo[3.1.0]hexane hydrochlorideHCID 118157877Ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate

Product 1

HCID 118157898Ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In DCM (50 mL) was dissolved the above product ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate. To the solution were added 3-azabicyclo[3.1.0]hexan hydrochloride salt (0.8 g, 6.67 mmol) and triethylamine (4 mL, 28.8 mmol). The reaction was conducted at ambient temperature for 18 h, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate, and the solvent was removed by rotary evaporation to give ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate as a faint yellow oil (3.1 g). The product was used in the subsequent procedure without further purification.

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-dab13fa911a0441e9141acf3f808f873
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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