Acetonitrile → N-(3-(5-(2-aminopyrimidin-5-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)phenyl)acetamide

HRID 1692798Notes

Reaction equation

HRID 1692798 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[N:8][C:6]=2[N:7]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+].[C:37](#[N:39])[CH3:38]>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.O>[NH2:7][C:2]1[N:3]=[CH:4][C:38]([C:2]2[N:3]=[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:5]3[S:10][C:9]([C:26]4[CH:27]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:23]=[CH:24][CH:25]=4)=[N:8][C:6]=3[N:7]=2)=[CH:37][N:39]=1

Participants

7

Reactant 4

HCID 6342Acetonitrile2×HCID 10340Sodium Carbonate2×HCID 157274(3-Acetamidophenyl)boronic acidHCID 252527634-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Product 1

HCID 25254935N-(3-(5-(2-aminopyrimidin-5-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×

Procedure

4-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine 27, 3-acetamido-phenyl 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 90° C. for 10 minutes. Water was added and the solution was filtered. The aqueous layer was dried and combined with 5-pyrimidine-2-amine boronic acid (1.2 eq) and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) and slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 150° C. for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was purified by reverse phase silica gel chromatography to yield 140.

Workup

  1. customThe solution was microwaved at 90° C. for 10 minutes
  2. filtrationthe solution was filtered
  3. customThe aqueous layer was dried
  4. customThe solution was microwaved at 150° C. for 10 minutes
  5. filtrationthe solution was filtered
  6. customThe resulting precipitate was purified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-46b9947e83c44960981fe832428ce62d
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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