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Sodium Carbonate → 5-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876623
Notes
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Reaction equation

HRID 1876623 reaction equation
O1CCOCC1.Cl[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH2:17][CH:18]([CH3:20])[CH3:19])=[C:10]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][C@@H:22]2[CH3:27])[N:9]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][C:39]([NH2:42])=[N:40][CH:41]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:17]([N:14]1[CH:13]=[N:12][C:11]2[C:15]1=[N:16][C:8]([C:36]1[CH:37]=[N:38][C:39]([NH2:42])=[N:40][CH:41]=1)=[N:9][C:10]=2[N:21]1[CH2:26][CH2:25][O:24][CH2:23][C@@H:22]1[CH3:27])[CH:18]([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 593335472-Chloro-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine

Product 1

HCID 593335335-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-2-yl}pyrimidin-2-amineYield 76.4%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent2×

Procedure

A dioxane (5 ml)-water (1 ml) suspension of 2-chloro-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine (317 mg, 1.02 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (226 mg, 1.02 mmol), sodium carbonate (325 mg, 3.07 mmol), and tetrakis triphenylphosphine palladium (118 mg, 0.10 mmol) was heated to reflux for 2.5 hours. The reaction mixture was returned to room temperature. Water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=96:4). The residue was purified by flash silica gel column chromatography (ethyl acetate) to give the title compound (287 mg, 76%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. customwas returned to room temperature
  4. extractionthe resulting mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationafter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=96:4)
  9. customThe residue was purified by flash silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-491fc0c3dbd94be698058d61be5a7830
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309546B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes