Acetonitrile → HCID 25254456, compound

HRID 1692776Notes

Reaction equation

HRID 1692776 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:34](#[N:36])[CH3:35]>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>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:8][C:6]3[N:7]=[C:2]([C:35]4[CH:34]=[N:36][C:2]([NH2:7])=[N:3][CH:4]=4)[N:3]=[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:5]=3[N:10]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 445416755-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Product 1

HCID 25254456HCID 25254456, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine, 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 (3 eq) and acetonitrile. The solution was microwaved at 130° C. for 8 minutes. The solvents were removed and the resulting residue was purified by reverse phase silica gel chromatography to give 122.

Workup

  1. customThe solution was microwaved at 130° C. for 8 minutes
  2. customThe solvents were removed
  3. customthe resulting residue was purified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-bfd6e81faccf40bbb49c0cf9f705d98f
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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