Acetonitrile → 2-(5-(2-Aminopyrimidin-5-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)propan-2-ol

HRID 1692793Notes

Reaction equation

HRID 1692793 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:27](#[N:29])[CH3:28]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:7][C:2]1[N:3]=[CH:4][C:28]([C:2]2[N:3]=[C:4]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:5]3[S:10][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:8][C:6]=3[N:7]=2)=[CH:27][N:29]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 866300812-(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)propan-2-ol

Product 1

HCID 252549322-(5-(2-Aminopyrimidin-5-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)propan-2-ol, 5-pyrimidine-2-amine boronic acid (1.2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 130° C. for 15 minutes. The solution was evaporated to dryness and purified by reverse phase silica gel chromatography to give the product 137.

Workup

  1. customThe solution was microwaved at 130° C. for 15 minutes
  2. customThe solution was evaporated to dryness
  3. custompurified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-c98ee62f56044c28a63f7f770575c21f
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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