Triethylamine → HCID 118390102, compound

HRID 1478012Notes

Reaction equation

HRID 1478012 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][CH:11]1[CH2:19][CH2:18][CH:17]2[CH:13]([CH2:14][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)[CH2:12]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH:11]2[CH2:19][CH2:18][CH:17]3[CH:13]([CH2:14][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]3)[CH2:12]2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 83487964TERT-BUTYL 5-AMINOOCTAHYDRO-2H-ISOINDOLE-2-CARBOXYLATE

Product 1

HCID 118390102HCID 118390102, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,5-trichloropyrimidine (0.60 g, 3.27 mmol) and tert-butyl 5-aminohexahydro-1H-isoindole-2(3H)-carboxylate (2.79 g, 11.61 mmol) in EtOH (10 mL) was added Et3N (1.30 g, 12.84 mmol). After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as a pale yellow solid (1.60 g, 100%).

Workup

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

Sources & evidence

ORD record
ord-8d406dbfe6f844edb3022b74cba2c00c
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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