Ammonium formate → HCID 178481006, compound

HRID 432298Notes

Reaction equation

HRID 432298 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[N:21][C:22]=3[NH2:24])[N:17]([C@H:25]3[CH2:30][CH2:29][C@@H:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[CH2:27][CH2:26]3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:24][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:17]([C@H:25]3[CH2:30][CH2:29][C@@H:28]([N:31]4[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]4)[CH2:27][CH2:26]3)[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:23]=12

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178481008HCID 178481008, compound

Product 1

HCID 178481006HCID 178481006, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of cis-3-[4-(benzyloxy)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.500 g, 1.005 mmol) in absolute ethanol (25 mL) was treated with palladium 10 wt. % on activated carbon (0.100 g, 0.201 mmol) and ammonium formate (0.317 g, 5.03 mmol). The reaction mixture was stirred at 80° C. for 2 h; no starting material was seen by thin layer chromatography. The reaction mixture was filtered through a pad of celite, which was washed with ethanol (500 mL). The organic layer was removed under reduced pressure. The resulting solid was dried over night under high vacuum to give 0.406 g (99%) of cis-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol. 1H NMR (DMSO-d6, 400 MHz) δ 8.204-8.194 (m, 2H), 7.472-7.437 (m, 2H), 6.947-6.912 (m, 2H), 4.791-4.744 (m, 1H), 2.418 (m, 9H), 2.249-2.243 (m, 2H), 2.193 (s, 3H), 2.077-2.050 (m, 2H), 1.688-1.666 (m, 2H), 1.656-1.578 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 3.47 min (99%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite, which
  2. washwas washed with ethanol (500 mL)
  3. customThe organic layer was removed under reduced pressure
  4. customThe resulting solid was dried over night under high vacuum

Sources & evidence

ORD record
ord-067ffa38e9524a36a7a4adb85246a11b
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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