Ammonium Bicarbonate → HCID 11562553, compound

HRID 502642Notes

Reaction equation

HRID 502642 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]2[C:18]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:24]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][N:41]5[CH2:45][CH2:44][CH2:43][CH2:42]5)=[CH:34][CH:33]=4)[O:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(=O)(O)[O-].[NH4+]>CO.[Pd]>[C:26]1([C:25]2[C:18]3[C:17]([NH:16][CH2:15][CH2:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[N:22][CH:21]=[N:20][C:19]=3[O:23][C:24]=2[C:32]2[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][N:41]3[CH2:42][CH2:43][CH2:44][CH2:45]3)=[CH:36][CH:37]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14013Ammonium BicarbonateHCID 58603249HCID 58603249, compound

Product 1

HCID 11562553HCID 11562553, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(2-(1-benzylpiperidin-4-yl)ethyl)-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4-amine 29 (Prepared in a manner analogous to Steps 1-3 of Example 5; 20 mg, 0.033 mmol), ammonium bicarbonate (−30 mg, 0.5 mmol) and 10% Pd/C (˜5 mg) were taken up in MeOH (3-5 mL). The mixture was heated at reflux for 48 h, then filtered through a pad of Celite, washing with MeOH and EtOAc and concentrated. Preparative TLC (SiO2, 15% MeOH in CH2Cl2) afforded the title compound 30. Mass for C31H37N5O2 found: 512 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. filtrationfiltered through a pad of Celite
  4. washwashing with MeOH and EtOAc
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99f10115bf884a33b148f2979e836de9
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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