Ammonia → HCID 67055613, compound

HRID 604992Notes

Reaction equation

HRID 604992 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12.[NH3:24]>C(O)C>[NH2:24][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate

Product 1

HCID 67055613HCID 67055613, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (0.050 g, 0.148 mmol) in ethanol saturated with ammonia (1 mL) was heated to 80° C. for 30 min. in a sealed tube in the microwave. The mixture was cooled, concentrated, and dried in vacuo to give tert-butyl 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate which was used without further purification. 1H-NMR (500 MHz, CDCl3) δ 8.38 (s, 1H), 7.93 (s, 1H), 5.60 (bs, 2H), 4.84-4.95 (m, 1H), 4.29 (bs, 2H), 2.95 (bs, 2H), 2.13-2.28 (m, 2H), 1.92-2.03 (m, 2H). LRMS m/z (M+H) Calcd: 319.1, found: 319.1.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-6554b2249c574aeb8dac9736d4abdf51
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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