Pyridine → (R,R)-4-Ethyl-6-[1-(1-phenyl-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl]-pyrimidin-2-ylamine

HRID 2360571Notes

Reaction equation

HRID 2360571 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.N1C=CC=CC=1.[C:17]1([CH:23]([N:25]2[CH2:29][CH2:28][CH:27]3[CH2:30][NH:31][CH2:32][CH:26]23)[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCO>[CH2:8]([C:6]1[CH:7]=[C:2]([N:31]2[CH2:30][C@@H:27]3[C@@H:26]([N:25]([CH:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:24])[CH2:29][CH2:28]3)[CH2:32]2)[N:3]=[C:4]([NH2:10])[N:5]=1)[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 223243042-Amino-4-chloro-6-ethylpyrimidineHCID 22646884(3aS,6aS)-1-((R)-1-Phenylethyl)octahydropyrrolo[3,4-b]pyrrole

Product 1

HCID 67096362(R,R)-4-Ethyl-6-[1-(1-phenyl-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl]-pyrimidin-2-ylamineYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-6-ethyl-pyrimidin-2-ylamine (200 mg, 1.27 mmol) in EtOH (2.4 mL) was added pyridine (210 μL, 2.54 mmol) and 1-(1-phenyl-ethyl)-octahydro-pyrrolo[3,4-b]pyrrole (360 mg, 1.65 mmol). The solution was stirred for 2 h at 90° C. The compound was purified directly with reversed-phase HPLC to yield 115 mg (28%) of the desired compound as a yellow oil.

Workup

  1. customThe compound was purified directly with reversed-phase HPLC

Sources & evidence

ORD record
ord-f39dd3f2cfa847d18f5c5b761c5350dd
Source dataset
uspto-grants-2014_04
Patent number
US08686142B2

Reaction notes

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