N,N-Bis(trimethylsilyl)trifluoroacetamide → 3-[[5-{5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-5-[2-methoxyethoxymethyl]benzoic acid, ethyl ester

HRID 1531919Notes

Reaction equation

HRID 1531919 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[CH2:39]([O:41][C:42](=[O:57])[C:43]1[CH:48]=[C:47]([CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[CH:46]=[C:45]([CH2:55]Br)[CH:44]=1)[CH3:40]>ClCCCl>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[N:20]([CH2:55][C:45]4[CH:44]=[C:43]([CH:48]=[C:47]([CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[CH:46]=4)[C:42]([O:41][CH2:39][CH3:40])=[O:57])[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedioneHCID 702251523-Bromomethyl-5-[2-methoxyethoxymethyl]benzoic acid ethyl ester

Product 1

HCID 1317224283-[[5-{5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-5-[2-methoxyethoxymethyl]benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of example 2 step (ii) (0.41 g) and bis[trimethylsilyl]trifluoroacetamide (0.73 g) in 1,2-dichloroethane (10 ml) was heated at reflux for 1 hour. The product from step (i) (0.45 g) was added and the mixture was heated at reflux for 7 hours. The mixture was evaporated and the residue purified by chromatography eluting with 30% ethyl acetate in isohexane. Yield 0.52 g.

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 7 hours
  4. customThe mixture was evaporated
  5. customthe residue purified by chromatography
  6. washeluting with 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f5d728d4eaa54751a9796d53a8ad04a5
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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