1-tert-butyl-3-(3-(benzyloxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine → HCID 178508712, compound

HRID 731876Notes

Reaction equation

HRID 731876 reaction equation
C([N:5]1[C:9]2=[N:10][CH:11]=[N:12][C:13]([NH2:14])=[C:8]2[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)=[N:6]1)(C)(C)C.NC1N=CN=C2NN=C(C3C=C(O)C=CC=3)C=12>C(O)=O.Cl>[CH2:22]([O:21][C:17]1[CH:16]=[C:15]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[N:12][C:13]=3[NH2:14])[NH:5][N:6]=2)[CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 99514401-tert-butyl-3-(3-(benzyloxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 178508710HCID 178508710, compound

Product 1

HCID 178508712HCID 178508712, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

1-tert-butyl-3-(3-(benzyloxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (19 mg, 0.052 mmol) was dissolved in a solution of formic acid (1 mL) and conc. HCl (0.1 mL) and heated to reflux for 30 min. Reaction yielded a mixture of ZK136 and 3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol (ZK138). Reaction was concentrated in vacuo and the products purified by RP-HPLC (MeCN:H2O:0.1% TFA). ZK136: ESI-MS (M+H)+ m/z calcd 318.1, found 318.3. ZK138: ESI-MS (M+H)+ m/z calcd 228.1, found 228.3.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. customReaction
  4. customyielded
  5. customReaction
  6. concentrationwas concentrated in vacuo
  7. customthe products purified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-445c81f4e1724c31af410aca3c81b98e
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

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