Sodium Carbonate → 5-[6-Morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amine

HRID 1876497Notes

Reaction equation

HRID 1876497 reaction equation
O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=2)O1.Cl[C:30]1[N:38]=[C:37]2[C:33]([N:34]=[CH:35][N:36]2[CH2:39][CH:40]2[CH2:44][CH2:43][O:42][CH2:41]2)=[C:32]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)[N:31]=1>O.C(OCC)(=O)C>[N:45]1([C:32]2[N:31]=[C:30]([C:21]3[CH:26]=[N:25][C:24]([NH2:27])=[N:23][CH:22]=3)[N:38]=[C:37]3[C:33]=2[N:34]=[CH:35][N:36]3[CH2:39][CH:40]2[CH2:44][CH2:43][O:42][CH2:41]2)[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 593335062-Chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

Product 1

HCID 593335855-[6-Morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amineYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1,4-Dioxane (40 ml), water (20 ml), and sodium carbonate (3.6 g, 33.9 mmol) were added to 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (2.5 g, 11.3 mmol) and 2-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine (3.7 g, 11.3 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. Tetrakis triphenylphosphine palladium (0.65 g, 0.57 mmol) was added, then the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was heated to reflux for 2 hours. The reaction mixture was cooled followed by the addition of ethyl acetate and water and the insoluble matter was collected by filtration, then washed with ethyl acetate and water, and dried to give the title compound (2.6 g, 59%) as a pale orange solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe insoluble matter was collected by filtration
  5. washwashed with ethyl acetate and water
  6. customdried

Sources & evidence

ORD record
ord-4069877d05d146cd8869a906ff7b9293
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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