Acetonitrile → HCID 22349461, compound

HRID 896031Notes

Reaction equation

HRID 896031 reaction equation
[OH:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:13]3[C:9](=[CH:10][N:11]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)[N:12]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:26][O:27][CH2:28][CH2:29][C:30]1(Br)[C:35](=[O:36])[NH:34][C:33](=[O:37])[NH:32][C:31]1=[O:38].C1CN2C(=NCCC2)NC1.C(#N)C>CO.C(O)(=O)C>[CH:5]([O:6][CH:7]([CH3:15])[CH3:8])([CH3:24])[CH3:4].[CH3:26][O:27][CH2:28][CH2:29][C:30]1([O:1][C:2]2[CH:25]=[CH:24][C:5]([O:6][C:7]3[CH:15]=[CH:14][C:13]4[C:9](=[CH:10][N:11]([C:16]5[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=5)[N:12]=4)[CH:8]=3)=[CH:4][CH:3]=2)[C:31](=[O:38])[NH:32][C:33](=[O:37])[NH:34][C:35]1=[O:36]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 79873TriazabicyclodeceneHCID 219311515-Bromo-5-(2-methoxyethyl)pyrimidine-2,4,6(1H,3H,5H)-trioneHCID 22349441HCID 22349441, compound

Product 2

HCID 7914Diisopropyl EtherHCID 22349461HCID 22349461, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-[5-(4-Hydroxy-phenoxy)-indazol-2-yl]-benzonitrile (0.070 grams, 0.22 mmol), 2-methoxyethylbromobarbiturate (0.10 grams, 0.4 mmol), 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene (0.44 grams) and acetonitrile (2.3 mL) was shaken for 24 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 radial chromatography eluting with 3:2 ethyl acetate-hexanes. Trituration of the purified product with iso-propyl ether afforded 4-(5-{4-[5-(2-Methoxy-ethyl)-2,4,6-trioxo-hexahydro-pyrimidin-5-yloxy]-phenoxy}-indazol-2-yl)-benzonitrile (0.027 grams) as a colorless solid. MS: 512.7 [M+H]+; 510.6 [M−H]−

Workup

  1. stirringshaken for 20 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by radial chromatography
  5. washeluting with 3:2 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-16de8001ec4e4c1b9464d243517e15f5
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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