Sodium Carbonate → 5-[9-(Cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine

HRID 1876491Notes

Reaction equation

HRID 1876491 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH2:23][CH:24]2[CH2:26][CH2:25]2)=[C:16]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:15]=1.CC1(C)C(C)(C)OB([C:41]2[CH:42]=[N:43][C:44]([NH2:47])=[N:45][CH:46]=2)O1>C(OCC)(=O)C.O>[CH:24]1([CH2:23][N:20]2[CH:19]=[N:18][C:17]3[C:21]2=[N:22][C:14]([C:41]2[CH:42]=[N:43][C:44]([NH2:47])=[N:45][CH:46]=2)=[N:15][C:16]=3[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 593335522-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine

Product 1

HCID 593335755-[9-(Cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amineYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium carbonate (3.25 g, 30.6 mmol) and tetrakis triphenylphosphine palladium (0.59 g, 0.51 mmol) were added to a 1,4-dioxane (60.0 ml)-water (30.0 ml) mixture solution of 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine (3.0 g, 10.2 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (2.5 g, 11.2 mmol) at room temperature and the resulting mixture was heated to reflux for 3 hours in an argon atmosphere. The reaction mixture was left standing to cool and then poured into water, and ethyl acetate was added to separate the layers. The solid precipitated in the aqueous layer was collected by filtration, washed with water, and dried at 50° C. under reduced pressure to give the title compound (3.63 g, 100%) as a white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours in an argon atmosphere
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. additionwas added
  6. customto separate the layers
  7. customThe solid precipitated in the aqueous layer
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-d361f3bab9a64d59bcc37714e846dd2f
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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