Triazabicyclodecene → HCID 9893236, compound

HRID 1243965Notes

Reaction equation

HRID 1243965 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([C:13]2[CH:26]=[CH:25][C:16]([O:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:15][CH:14]=2)[O:11][CH:12]=1.C1CN2C(=NCCC2)NC1.Br[C:38]1([CH2:47][CH2:48][O:49][CH3:50])[C:43](=[O:44])[NH:42][C:41](=[O:45])[NH:40][C:39]1=[O:46]>C(#N)C>[CH3:50][O:49][CH2:48][CH2:47][C:38]1([O:24][C:21]2[CH:22]=[CH:23][C:18]([O:17][C:16]3[CH:15]=[CH:14][C:13]([C:10]4[O:11][CH:12]=[C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])[N:9]=4)=[CH:26][CH:25]=3)=[CH:19][CH:20]=2)[C:39](=[O:46])[NH:40][C:41](=[O:45])[NH:42][C:43]1=[O:44]

Participants

5

Reactant 3

HCID 79873TriazabicyclodeceneHCID 21931143HCID 21931143, compoundHCID 219311515-Bromo-5-(2-methoxyethyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Product 1

HCID 9893236HCID 9893236, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[4-(4-(2-fluorophenyl)-oxazol-2-yl)-phenoxy]-phenol (142 mg, 0.41 mmol), and 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (Fluka) (473 mg @ 2.6 meq/g, 1.23 meq) in acetonitrile were shaken for 30 minutes. 5-Bromo-5-(2-methoxy-ethyl)-pyrimidine-2,4,6-trione (163 mg, 0.62 mmol) (from Preparation 3b) was then added and shaking continued for 3 days. The reaction was quenched with 20% acetic acid in methanol and after 15 minutes filtered. The filtrate was concentrated and the crude product chromatographed yielding 145 mg of 5-(2-methoxy-ethyl)-5-{4-[4-(4-(2-fluorophenyl)-oxazol-2-yl)-phenoxy]-phenoxy}-pyrimidine-2,4,6-trione as a white solid. LC-MS (m/z, APCI): 533 [M+H]+.

Workup

  1. stirringshaking
  2. waitcontinued for 3 days
  3. customThe reaction was quenched with 20% acetic acid in methanol and after 15 minutes
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe crude product chromatographed

Sources & evidence

ORD record
ord-587b9bd6bb3e403db12453b52796a308
Source dataset
uspto-grants-2006_10
Patent number
US07119201B2

Reaction notes

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