Acetic Acid → 4-Amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidine-3-carbaldehyde

HRID 1499845Notes

Reaction equation

HRID 1499845 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:15]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([CH3:24])=[C:19]([Br:25])[C:18]=3[O:26][CH3:27])[CH3:16])[N:9]=[C:10]([CH:11]([OH:14])CO)[C:3]=12.C(O)(=O)C.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:15]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([CH3:24])=[C:19]([Br:25])[C:18]=3[O:26][CH3:27])[CH3:16])[N:9]=[C:10]([CH:11]=[O:14])[C:3]=12

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23667635Sodium periodateHCID 866777681-{4-Amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethane-1,2-diol

Product 1

HCID 866777694-Amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{4-amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethane-1,2-diol (0.10 g, 0.22 mmol) in tetrahydrofuran (1.6 mL)/water (1.0 mL) was added acetic acid (0.0032 mL, 0.057 mmol) and sodium periodate (0.140 g, 0.657 mmol) at 0° C. After stirring for 2 h, the reaction mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give the desired crude product which was used directly in the next step. LCMS calculated for C16H16BrClN5O2 (M+H)+: m/z=424.0; Found: 423.9

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-446cb8769a244c169c14154157b1572e
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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