Triethylamine → HCID 24855094, compound

HRID 1689936Notes

Reaction equation

HRID 1689936 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[S:23][CH:22]=[CH:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)[N:13]=2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:25][NH:26][CH3:27].C(N(CC)CC)C.O1CCOCC1>C(Cl)(Cl)Cl>[CH3:25][N:26]([CH3:27])[C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[S:23][CH:22]=[CH:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 312751,4-DioxaneHCID 24855050HCID 24855050, compound

Product 1

HCID 24855094HCID 24855094, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-[4-(2-fluoro-pyridin-4-yl)-thieno[3,2-d]pyrimidin-2-yl]-phenol, (60 mg), dimethylamine hydrochloride (151 mg), triethylamine (0.31 mL) and 1,4-dioxane (3 mL) was heated to 130° C. in a sealed tube. After heating for 24 hours the reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield the title compound (40 mg).

Workup

  1. temperatureAfter heating for 24 hours the reaction mixture
  2. temperaturewas cooled
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-33b75719a7c84dda91019e25cfd62fc6
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

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