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Potassium Carbonate → 3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester

HRID 1912395
Notes
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Reaction equation

HRID 1912395 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:14]2([CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH:13]([CH3:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:22]1[C:23]2[CH:30]=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:8][C:9]([N:11]1[C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:22]3[C:23]4[CH:30]=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:15]2)[CH:13]([CH3:20])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 582933243-Methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl ester

Product 1

HCID 582932883-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl esterYield 58.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

An optically-active compound of 3-methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl ester (108 mg) was mixed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (32 mg), potassium carbonate (86 mg) and water (2.1 ml), and stirred overnight with refluxing. The mixture was cooled to room temperature, and extracted with chloroform. The separated organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 0/1, followed by chloroform/methanol=9/1) to give the titled compound (48 mg).

Workup

  1. temperaturewith refluxing
  2. extractionextracted with chloroform
  3. washThe separated organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 0/1, followed by chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e1d89553f3e744dfb69dbdfcbc85e7c4
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609647B2

Reaction notes

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