Acetonitrile → HCID 10217587, compound

HRID 896024Notes

Reaction equation

HRID 896024 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][C:12]([O:16][C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)=[CH:13]3)=[N:8]2)[CH:2]=1.[CH3:24][O:25][CH2:26][CH2:27][C:28]1(Br)[C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30][C:29]1=[O:36].C1CN2C(=NCCC2)NC1.C(#N)C>CO.C(O)(=O)C>[CH:12]([O:16][CH:17]([CH3:22])[CH3:18])([CH3:13])[CH3:11].[CH3:24][O:25][CH2:26][CH2:27][C:28]1([O:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:12]3[CH:11]=[CH:10][C:9]4[C:14](=[CH:15][N:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[N:8]=4)[CH:13]=3)=[CH:18][CH:19]=2)[C:29](=[O:36])[NH:30][C:31](=[O:35])[NH:32][C:33]1=[O:34]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 79873TriazabicyclodeceneHCID 219311515-Bromo-5-(2-methoxyethyl)pyrimidine-2,4,6(1H,3H,5H)-trioneHCID 22349470HCID 22349470, compound

Product 2

HCID 7914Diisopropyl EtherHCID 10217587HCID 10217587, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-(2-Pyridin-3-yl-2H-indazol-5-yloxy)-phenol (0.05 grams, 0.17 mmol), 2-methoxyethylbromobarbiturate (0.06 grams, 0.2 mmol), 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene (0.22 grams) and acetonitrile (1.5 mL) was shaken for 48 hours at room temperature. The mixture was treated with a solution of acetic acid in methanol (1:4 v/v), shaken for 20 minutes, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography eluting with an ethyl acetate-hexanes gradient (0-100% ethyl acetate). Trituration of the purified product with iso-propyl ether afforded 5-(2-Methoxy-ethyl)-5-[4-(2-pyridin-3-yl-2H-indazol-5-yloxy)-phenoxy]-pyrimidine-2,4,6-trione (0.009 grams) as a colorless solid.

Workup

  1. stirringshaken for 20 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with an ethyl acetate-hexanes gradient (0-100% ethyl acetate)

Sources & evidence

ORD record
ord-72d1991ebb404f6782f53842e89e0c2c
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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