Ethanol → HCID 118599009, compound

HRID 1050417Notes

Reaction equation

HRID 1050417 reaction equation
O1CCCC1.C(O)C.[Cl:9][C:10]1[C:11]([NH:35]C(C2CC2)=O)=[N:12][CH:13]=[N:14][C:15]=1[NH:16][C:17]1[C:22](=[O:23])[N:21]2[C:24]3([NH:31][C:32](=[O:33])[C:20]2=[C:19]([CH3:34])[CH:18]=1)[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3.[OH-].[Na+]>O>[NH2:35][C:11]1[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]2[C:22](=[O:23])[N:21]3[C:24]4([NH:31][C:32](=[O:33])[C:20]3=[C:19]([CH3:34])[CH:18]=2)[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[C:10]=1[Cl:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118598942HCID 118598942, compound

Product 1

HCID 118599009HCID 118599009, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A flask containing tetrahydrofuran, ethanol and water (1:1:1, 5 mL each) was charged with 6-((6-amino-5-methoxypyrimidin-4-yl)amino)-1′,8-dimethyl-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione (3, 0.17 g, 0.371 mmol) and sodium hydroxide (75 mg, 1.85 mmol). The reaction was stirred at 50° C. for 16 h. After completion, the reaction mass was extracted with 10% methanol in dichloromethane. Combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate concentrated under vacuum obtained solid was washed with ether and dried under vacuum to afford 6-((6-amino-5-chloropyrimidin-4-yl)amino)-1′,8-dimethyl-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione as light yellow solid. Yield: 88 mg, 31%; MS (ESI) m/z 390.14 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.16 (s, 1H), 8.52 (s, 1H), 8.50 (s, 1H), 8.17 (s, 1H), 7.10 (brs, 2H), 3.30-3.20 (m, 2H), 2.90-2.82 (brs, 2H), 2.49-2.40 (m, 2H), 2.46 (s, 3H), 2.30 (s, 3H), 1.46-1.40 (m, 2H).

Workup

  1. extractionAfter completion, the reaction mass was extracted with 10% methanol in dichloromethane
  2. washCombined organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customobtained solid
  6. washwas washed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7270f553cfce41afbdaaf132cd41eeed
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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