Tetrahydrofuran → 4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehyde

HRID 421442Notes

Reaction equation

HRID 421442 reaction equation
[O:1]1CCC[CH2:2]1.[CH2:6]([N:10]1[C:18]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:32]1[CH:33]=[N:34][C:35]([NH2:38])=[N:36][CH:37]=1)=[N:14][C:15]=2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]1[CH3:31])[CH:7]([CH3:9])[CH3:8].N1(C=O)C2C=CC=CC=2N=N1.[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[NH2:38][C:35]1[N:36]=[CH:37][C:32]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:18]([N:19]4[CH2:24][CH2:23][N:22]([CH:2]=[O:1])[CH2:21][CH2:20]4)[N:10]3[CH2:6][CH:7]([CH3:9])[CH3:8])=[C:15]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]3[CH3:31])[N:14]=2)=[CH:33][N:34]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 593335555-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine

Product 1

HCID 593336504-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehydeYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A tetrahydrofuran (3 ml) solution of 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (103 mg, 0.23 mmol) and 1H-benzotriazole-1-carboaldehyde (37 mg, 0.25 mmol) was stirred at room temperature for 16 hours. Chloroform and 2 N aqueous sodium hydroxide solution were 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=95:5) to give a solid. Ether was added to the resulting solid and the solid was collected by filtration and dried to give the title compound (86 mg, 79%) as a powder.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationafter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5)
  6. customto give a solid
  7. filtrationthe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-aeba426967964679bde3c18251135089
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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