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3,4,5-Trimethoxyaniline → 2-(3,4,5-Trimethoxyphenylamino)-3-acetamido-6-(3-acetamidophenyl)pyrazine

HRID 16274
Notes
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Reaction equation

HRID 16274 reaction equation
Br[C:2]1[C:7]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=2)[N:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[NH2:27].CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:34][O:33][C:29]1[CH:28]=[C:26]([NH:27][C:2]2[C:7]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=3)[N:3]=2)[CH:25]=[C:24]([O:23][CH3:22])[C:30]=1[O:31][CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 322853,4,5-TrimethoxyanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 593434502-Bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine

Product 1

HCID 115832652-(3,4,5-Trimethoxyphenylamino)-3-acetamido-6-(3-acetamidophenyl)pyrazineYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Method AA. In a tube suitable for microwave irradiation provided with stirring and an argon atmosphere were placed 2-bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine (32 mg, 0.09164 mmol), 3,4,5-trimethoxyaniline (33.6 mg, 0.1833 mmol), sodium tert-butoxide (18 mg, 0.1833 mmol), Pd(0)2 dba3 (8.4 mg, 9.164 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xant phos) (5.3 mg, 9.164 μmol) and dry toluene 1.5 mL). The tube was heated by microwave irradiation at 110° C. for 30 minutes. The reaction crude was filtered and the precipitate washed with boiling ethyl acetate (30 mL). The organic layers were evaporated under vacuum and the resulting crude was chromatographed (eluent: mixture of ethyl acetate and methanol; 9:1) to produce 7 mg of title compound. Yield: 17%. 1H NMR (250 MHz, DMSO-d6) δ 2.06 (s, 3H), 2.17 (s, 3H), 3.64 (s, 3H), 3.77 (s, 9H), 7.24 (s, 2H), 7.42 (t, 1H, J=8.0 Hz), 7.64 (d, 1H, J=7.7 Hz), 7.73 (d, 1H, J=7.9 Hz), 8.22 (bs, 1H), 8.28 (s, 1H), 8.52 (s, 1H), 10.07 (s, 1H), 10.21 (s, 1H). m/z 452.2 [(M+H)+ calcd for C23H25N5O5 451.2].

Workup

  1. customIn a tube suitable for microwave irradiation
  2. customprovided
  3. customThe reaction crude
  4. filtrationwas filtered
  5. washthe precipitate washed with boiling ethyl acetate (30 mL)
  6. customThe organic layers were evaporated under vacuum
  7. customthe resulting crude was chromatographed
  8. addition(eluent: mixture of ethyl acetate and methanol; 9:1)

Sources & evidence

ORD record
ord-ea0bc40c44714cc5bd7c3c70baec4e8f
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737152B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes