Triethylamine → HCID 83401227, compound

HRID 1255198Notes

Reaction equation

HRID 1255198 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.C(N(CC)CC)C.C(O[CH:20]=[C:21]([C:27](=O)[C:28]([F:31])([F:30])[F:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([N:8]2[C:27]([C:28]([F:29])([F:30])[F:31])=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]=[N:9]2)[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoateHCID 160921982-Chloro-4-hydrazinylpyrimidine

Product 1

HCID 83401227HCID 83401227, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 2-chloro-6-hydrazinopyrimidine (1.00 g, 6.92 mmol) and triethylamine (0.964 mL, 6.92 mmol) in acetonitrile (35 mL) was added ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate (1.35 mL, 6.97 mmol). After 45 min, the reaction mixture was placed in a 90° C. oil bath. After 1 h, the reaction mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes, then 60 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 321.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.80 (d, J=5.5 Hz, 1H), 8.12 (s, 1H), 7.76 (d, J=5.5 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

Workup

  1. customwas placed in a 90° C.
  2. waitAfter 1 h
  3. concentrationwas concentrated in vacuo
  4. customPurification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-3f65b2cddcc246aa8635eb72292dbedf
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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