2-Chlorophenol → 4-(1-(2-Chlorophenoxy)ethyl)-6-(methylthio)-1,3,5-triazin-2-amine

HRID 1845868Notes

Reaction equation

HRID 1845868 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1O.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>O1CCCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:12][CH:10]([C:4]1[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([NH2:1])[N:3]=1)[CH3:11]

Participants

6

Reactant 4

HCID 72452-ChlorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 672579331-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol

Product 1

HCID 672552294-(1-(2-Chlorophenoxy)ethyl)-6-(methylthio)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol (203 mg) in dry tetrahydrofuran (8 mL) was added 2-chlorophenol (0.122 mL) and triphenylphosphine (314 mg) followed by diisopropyl azodicarboxylate ((0.233 mL) dropwise. The solution was stirred at room temperature for 80 min then was concentrated in vacuo, dissolved in ethyl acetate (40 mL) and washed with 1N sodium hydroxide solution (2×40 mL), dried over sodium sulfate and concentrated to give a yellow oil. Purification by SCX chromatography eluting with a 1:1 mixture of dichloromethane-methanol then 2N ammonia in 1:1 mixture of dichloromethane-methanol followed by flash column chromatography, with 1% acetonirile in dichloromethane to give the title compound (207 mg).

Workup

  1. concentrationthen was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate (40 mL)
  3. washwashed with 1N sodium hydroxide solution (2×40 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by SCX chromatography
  8. washeluting with a 1:1 mixture of dichloromethane-methanol
  9. addition2N ammonia in 1:1 mixture of dichloromethane-methanol

Sources & evidence

ORD record
ord-5111969aae5a4d4b959c50b867b50200
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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