Water → HCID 22135426, compound

HRID 1826726Notes

Reaction equation

HRID 1826726 reaction equation
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH:22]1[C:30]2[C:25](=[C:26]([C:31]3[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.[OH2:38]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[NH2:37][C:34]1[N:35]=[CH:36][C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:25]=2[CH2:24][C:23](=[O:38])[NH:22]3)=[CH:32][N:33]=1

Participants

8

Reactant 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 22135460HCID 22135460, compound

Product 1

HCID 22135426HCID 22135426, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

Pyridinium tribromide (90% purity from Aldrich, 7.1 g, 19.98 mmol) was added in portions over 10 minutes to a suspension of 5-(1H-indol-4-yl)-pyrimidin-2-ylamine (1.4 g, 6.66 mmol) in 2-methyl-2-propanol (50 mL), ethanol (30 mL) and acetic acid (18 mL). The mixture was stirred at room temperature for 2 hours, and then acetic acid (72 mL), water (1 mL) and zinc (6.5 g, 100 mmol) were added. Stirring was continued for 1.5 hours. The unreacted zinc dust was filtered off and washed with methanol. The filtrate was concentrated and the syrupy residue was suspended in water (100 mL) overnight. The solid which formed was filtered off. The filtrate was basified with aqueous sodium bicarbonate and extracted with ethanol:dichloromethane (5:95) to give 4-(2-amino-pyrimidin-5-yl)-1,3-dihydro-indol-2-one.

Workup

  1. stirringStirring
  2. waitwas continued for 1.5 hours
  3. filtrationThe unreacted zinc dust was filtered off
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated
  6. waitthe syrupy residue was suspended in water (100 mL) overnight
  7. customThe solid which formed
  8. filtrationwas filtered off
  9. extractionextracted with ethanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-12a57c96c72c4183bba1ae83f82fbb57
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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