Hydrochloric Acid → Triethylamine hydrochloride

HRID 340162Notes

Reaction equation

HRID 340162 reaction equation
O=[C:2]1[NH:10][C:5]2[N:6]=[CH:7][N:8]=[CH:9][C:4]=2[C@:3]21[CH2:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([C:19]([O:21]C)=[O:20])[CH:16]=1)[CH2:11]2.[ClH:23].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].[Li+:31].[OH-:32].Cl>C1COCC1.CO>[O:32]=[C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][C@@:3]3([CH2:11]2)[C:4]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[NH:10][CH2:2]3)=[CH:16][CH:15]1[C:19]([OH:21])=[O:20].[Cl-:23].[Li+:31].[ClH:23].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11130Triethylamine hydrochlorideHCID 69965261Methyl (2R)-6'-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

Product 3

HCID 11130Triethylamine hydrochlorideYield 555.5%HCID 433294Lithium ChlorideHCID 86698226(2R)-6-oxo-1,3,6',7'-tetrahydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of a mixture of methyl (2R)-6′-oxo-1,3,6′,7′-tetrahydrospiro[indene-2,5′-pyrrolo[2,3-d]pyrimidine]-5-carboxylate (10 mg, 0.034 mmol) and triethylamine hydrochloride (0.034 mmol from previous step) in 1 mL of 1:1 THF/MeOH was added 1N LiOH (102 uL, 102 mmol). After 16 h, the reaction was neutralized to pH=7 with 3N HCl and then concentrated in vacuo. The crude material was azeotroped from benzene to afford the title compound as a mixture with 3 eq. of lithium chloride and 1 eq. triethylamine hydrochloride (13 mg). MS 282.1 (M+1). 1H NMR (500 MHz, DMSO d6): δ 11.57 (s, 1H); 8.69 (s, 1H); 8.11 (s, 1H); 7.84 (m, 2H); 7.40 (dd, J=8.3 Hz, 1H); 3.34-3.28 (m, 4H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was azeotroped from benzene

Sources & evidence

ORD record
ord-1a784bd0850346d991143b1fe22777f2
Source dataset
uspto-grants-2014_11
Patent number
US08895572B2

Reaction notes

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