Hydrochloric Acid → 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1909934Notes

Reaction equation

HRID 1909934 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:27])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)[C:3]=12.Cl>O1CCOCC1>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:10]3[C:3]4[C:4](=[N:5][CH:6]=[N:7][C:2]=4[NH2:1])[N:8]([CH3:27])[N:9]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668237181,1-dimethylethyl 5-(4-amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 668235513-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 250 mL round bottom flask, 1,1-dimethylethyl 5-(4-amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (745 mg, 2.033 mmol) was added followed by 4 M HCl in dioxane (12.2 mL). The mixture was stirred overnight at room temperature. LCMS showed no more SM. The light brown colored solid in the reaction mixture was filtered, washed by 20 mL of EtOAc, dried to give the desired product as a off-white solid. LC/MS (ES) m/z=267.1 [M+H]+

Workup

  1. filtrationThe light brown colored solid in the reaction mixture was filtered
  2. washwashed by 20 mL of EtOAc
  3. customdried

Sources & evidence

ORD record
ord-007ad0a488e04a85a394c3e021a6410a
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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