Acetonitrile → 5-(2-(3-(Methylsulfonyl)phenyl)-7-morpholinothiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine

HRID 1365827Notes

Reaction equation

HRID 1365827 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.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20].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>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([C:9]2[S:10][C:5]3[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:3][C:2]([C:38]4[CH:37]=[N:39][C:2]([NH2:7])=[N:3][CH:4]=4)=[N:7][C:6]=3[N:8]=2)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 6342Acetonitrile2×HCID 10340Sodium Carbonate2×HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 252527634-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Product 1

HCID 252549375-(2-(3-(Methylsulfonyl)phenyl)-7-morpholinothiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×

Procedure

5-Chloro-2-iodo-7-morpholinothiazolo[4,5-d]pyrimidine, 3-(methylsulfonyl)phenyl boronic acid and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate (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) were 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 142.

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-0527709fff364d389f3323ce71cadf71
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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