Ethyl orthoformate → HCID 178505656, compound

HRID 1710717Notes

Reaction equation

HRID 1710717 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:21])[C:11]([NH2:20])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH:22](OCC)(OCC)OCC>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[NH:21][CH:22]=[N:20][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 16070570HCID 16070570, compound

Product 1

HCID 178505656HCID 178505656, compoundYield 44%

Conditions

Temperature
140 °C

Procedure

A mixture of 5-(3-fluorophenyl)-6-pyridin-4-ylpyrazine-2,3-diamine (Example 72, 300 mg, 1.07 mmol) in 1,1′,1″-[methanetriyltris(oxy)]triethane (3 mL) was stirred and heated at 140° C. overnight. The solvent was removed under vacuum and the residue was triturated with diethyl ether. The resulting solid was purified by silica gel column chromatography (CH2Cl2/MeOH 9:1) to afford the title compound as a yellow solid (136 mg, 44%)

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with diethyl ether
  3. customThe resulting solid was purified by silica gel column chromatography (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-c46ac35ecb124495881e60123eb99f13
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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