Triethylamine → Triethylamine hydrochloride

HRID 340161Notes

Reaction equation

HRID 340161 reaction equation
[Cl:1][C:2]1[C:3]2[C@@:10]3([CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=4)[CH2:11]3)[C:9](=[O:23])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>CCOC(C)=O.[Pd]>[O:23]=[C:9]1[NH:8][C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[C@:10]21[CH2:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=1)[CH2:11]2.[ClH:1].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 86695346Methyl (2R)-4'-chloro-6'-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

Product 2

HCID 11130Triethylamine hydrochlorideYield 100.2%HCID 69965261Methyl (2R)-6'-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2R)-4′-chloro-6′-oxo-1,3,6′,7′-tetrahydrospiro[indene-2,5′-pyrrolo[2,3-d]pyrimidine]-5-carboxylate (860 mg, 2.61 mmol) and triethylamine (364 uL, 2.61 mmol) in 10 mL of EtOAc was added 2.6 g of 10% Pd—C in a Parr vessel. The reaction was placed on the Parr shaker at 50 psi H2. After 16 h, the reaction was backfilled with nitrogen, filtered through celite and concentrated in vacuo to afford the title compound as a mixture with 1 eq. triethylamine hydrochloride (360 mg). MS 296.1 (M+1).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07d7033865ae435890d75cf5b75ae701
Source dataset
uspto-grants-2014_11
Patent number
US08895572B2

Reaction notes

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