Tetrahydrofuran → HCID 178503501, compound

HRID 230169Notes

Reaction equation

HRID 230169 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:3]=12.[CH:20]([N:23](CC)C(C)C)(C)C.[CH2:29]1[CH2:33][O:32]CC1>C(OCC)(=O)C.O>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[C:3]2[C:4](=[N:5][C:6]([S:8][CH3:9])=[N:7][C:2]=2[NH:23][CH2:20][C@@H:33]([OH:32])[CH3:29])[NH:10][N:11]=1

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 81531DiisopropylethylamineHCID 178503465HCID 178503465, compound

Product 1

HCID 178503501HCID 178503501, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (300 mg, 0.964 mmol) and N,N-diisopropylethyl amine (0.34 mL, 2 eq) in THF (5 mL) was added dropwise a solution of (S)-(+)-1-amino-2-propanaol (Aldrich) (0.217 g, 3 eq) in THF. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC analysis. The reaction mixture was diluted with ethyl acetate (150 mL) and water (70 mL). The organic layer was separated, washed with water (2×70 mL) and brine (1×70 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as an off-white solid (328 mg, (M+H)+=350).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×70 mL) and brine (1×70 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11eef501411040e5bb492735d0694b69
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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