Water → HCID 22135426, compound

HRID 988145Notes

Reaction equation

HRID 988145 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. 1H NMR (360 MHz, DMSO-d6) δ 10.46 (s, 1H, NH), 8.47 (s, 2H), 7.24 (t, J=7.6 Hz, 1H), 6.99 (d, J=7.6 Hz, 1H), 6.79 (d, J=7.6 Hz, 1H), 6.78 (s, 2H, NH2), 3.64 (s, 2H)

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-16092252a30c4bfd88a2b373216387af
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

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