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Trifluoroacetic acid → 7-Amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine

HRID 326557
Notes
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Reaction equation

HRID 326557 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[N:3]=1.FC(F)(F)C(O)=O.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>ClCCl>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:23][CH:24]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62493Pivaloyl chlorideHCID 1764074-(2-(7-Amino-2-(2-furyl)-(1,2,4)triazolo(2,3-a)-(1,3,5)triazin-5-yl-amino)ethyl)phenol

Product 1

HCID 157300227-Amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

7-Amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4-triazolo[1,5-a][1,3,5]triazine (1 g, prepared as described in Example 81) was suspended in dichloromethane (20 ml) and trifluoroacetic acid (20 ml) was added with stirring. Pivaloyl chloride (0.4 ml) was added dropwise at ambient temperature. The mixture was stirred for 2 hours and then the dichloromethane and trifluoroacetic acid was removed in vacuo. The residue was purified by chromatography on silica (100 g) eluting with dichloromethane containing methanol (5.0% v/v). The solid obtained (1.2 g) was crystallised from toluene and finally from isopropanol (25 ml) to give 7-amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine as a solid; m.p. 208°-210° C.; microanalysis, found: C, 59.6; H, 6.1; N, 21.7%; C21H24N7O3 0.5 C3H7OH requires C, 59.9; H, 6.0; N, 21.7%; NMR 1.06(d, ca 3H, (CH3)2CHOH), 1.3(s, 9H, CH3C), 2.9(t, 2H, CH2Ar), 3.55 (t, 2H, CH2N), 3.80(heptet, ca 0.5 H, (CH 3)2 CHOH), 6.68(dd, 1H, furyl-4H), 7.01 and 7.30 (A2B2 pattern, 4H, phenyl-H), 7.08 (d, 1H, furyl-3H) and 7.82(d, 1H, furyl-5H); m/e 422 (M+H)+.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customthe dichloromethane and trifluoroacetic acid was removed in vacuo
  3. customThe residue was purified by chromatography on silica (100 g)
  4. washeluting with dichloromethane
  5. additioncontaining methanol (5.0% v/v)
  6. customThe solid obtained (1.2 g)
  7. customwas crystallised from toluene and finally from isopropanol (25 ml)

Sources & evidence

ORD record
ord-f2011253ad974945a2b988b1bdd332ee
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05270311

Reaction notes

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