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Phenol → 2-Furan-2-yl-6-(3-phenoxy-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242912
Notes
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Reaction equation

HRID 2242912 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:33]=[C:16]2[C:17]([NH2:32])=[N:18][C:19]([C:21]#[C:22][CH2:23]CCC3C=CC=CC=3)=[CH:20][N:15]2[N:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.O>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:33]=[C:16]2[C:17]([NH2:32])=[N:18][C:19]([C:21]#[C:22][CH2:23][O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:20][N:15]2[N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 114507462-Furan-2-yl-6-(5-phenyl-pent-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Product 1

HCID 112328032-Furan-2-yl-6-(3-phenoxy-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenol (9.4 mg, 0.1 mmol) and 3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-prop-2-yn-1-ol (0.05 mmol, see Ex. 46 below which was prepared according to Example 3 above) in THF (1 mL) at 0° C. was treated with triphenyl phosphine (26 mg, 0.1 mmol) and diisopropyl azodicarboxylate (20 uL, 0.1 mmol). After 30 min at 0° C., the reaction was allowed to warm to room temperature and was stirred for an additional 14 hours. The reaction mixture was diluted with water and concentrated in vacuo. The aqueous phase was extracted with ethyl acetate, and the organic extract was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified using preparative HPLC (C18, H2O:MeCN gradient) to afford 2-furan-2-yl-6-(3-phenoxy-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine as a white powder. 1H NMR (300 MHz, DMSO-d6) δ 8.45 (s, 1H), 7.92 (d, 1H), 7.34 (br m, 2H), 7.34 (t, J=8.7 Hz, 2H) 7.14 (d, J=3 Hz, 1H), 7.0-7.1 (br m, 3H), 6.72 (dd, J=3.0, 1.8 Hz, 1H), 5.07 (s, 2H), MS: m/z 332 [M+1].

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-340d2f5870d84e40b2945049a2c0426e
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07674791B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes