Potassium Carbonate → HCID 118598760, compound

HRID 1050371Notes

Reaction equation

HRID 1050371 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:14]([C:15]#[C:16][Si](C)(C)C)=[CH:13][N:12]=[CH:11][N:10]=2)[C:5](=[O:21])[N:4]2[C:22]3([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[NH:23][C:24](=[O:25])[C:3]=12.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:14]([C:15]#[CH:16])=[CH:13][N:12]=[CH:11][N:10]=2)[C:5](=[O:21])[N:4]2[C:22]3([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[NH:23][C:24](=[O:25])[C:3]=12

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 123179178HCID 123179178, compound

Product 1

HCID 118598760HCID 118598760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with 8′-chloro-6′-((5-((trimethylsilyl)ethynyl)pyrimidin-4-yl)amino)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (5, 300 mg, 0.67 mmol) and methanol (20 mL) followed by addition of potassium carbonate (469 mg, 3.39 mmol) at room temperature and reaction mixture was stirred for 16 h. After completion, solvent was concentrated under reduced pressure and the resulting residue was further washed with water followed by diethyl ether and pentane to afford 8′-chloro-6′-((5-ethynylpyrimidin-4-yl)amino)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (Cpd. No. 144) as yellow solid. Yield: 100 mg, 40%; MS (ESI) m/z 370.09 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.99 (s, 1H), 8.90 (s, 1H), 8.70 (s, 2H), 5.22 (s, 1H), 2.90 (brs, 2H), 1.73-1.64 (m, 2H), 1.61-1.56 (m, 3H), 1.56-1.53 (m, 2H), 1.27 (m, 1H).

Workup

  1. customreaction mixture
  2. concentrationAfter completion, solvent was concentrated under reduced pressure
  3. washthe resulting residue was further washed with water

Sources & evidence

ORD record
ord-b2984c04eaee46ae9dc89642a6b14d9c
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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