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Hydrochloric Acid → 1'-(9-Methyl-8-pyrimidin-5-yl-9H-purin-6-yl)spiro[indole-3,4'-piperidin]-2(1H)-one

HRID 528054
Notes
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Reaction equation

HRID 528054 reaction equation
[NH2:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][C:13]3([C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][C:16]3=[O:24])[CH2:12][CH2:11]2)=[N:4][CH:5]=[N:6][C:7]=1[NH:8][CH3:9].[N:25]1[CH:30]=[C:29]([CH:31]=O)[CH:28]=[N:27][CH:26]=1.Cl>C(O)C>[CH3:9][N:8]1[C:31]([C:29]2[CH:30]=[N:25][CH:26]=[N:27][CH:28]=2)=[N:1][C:2]2[C:7]1=[N:6][CH:5]=[N:4][C:3]=2[N:10]1[CH2:11][CH2:12][C:13]2([C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])[CH2:14][CH2:15]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2761034Pyrimidine-5-carboxaldehydeHCID 86711715HCID 86711715, compound

Product 1

HCID 668024531'-(9-Methyl-8-pyrimidin-5-yl-9H-purin-6-yl)spiro[indole-3,4'-piperidin]-2(1H)-oneYield 28.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1′-[5-amino-6-(methylamino)pyrimidin-4-yl]spiro[indole-3,4′-piperidin]-2(1H)-one (100 mg, 0.30 mmol) in anhydrous ethanol (12 mL) were added pyrimidine-5-carbaldehyde (38 mg, 0.35 mmol, Apollo Scientific Ltd.) and catalytic amount of hydrochloric acid (0.05 mL, 4N, Dioxane, Aldrich). The reaction mixture was heated to 80° C. for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 35.0 mg (28% yield) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)

Sources & evidence

ORD record
ord-7cb52b0dd837471d9e75daf520266a5f
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346807B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes