Ammonia → HCID 57928042, compound

HRID 657165Notes

Reaction equation

HRID 657165 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:11][N:10]=[C:9](/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]=1)(=O)=O.[NH3:30]>O1CCOCC1>[C:22]1(/[CH:21]=[CH:20]/[C:9]2[N:8]=[C:7]([NH2:30])[C:12]([O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)=[CH:11][N:10]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57927931HCID 57927931, compound

Product 1

HCID 57928042HCID 57928042, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Crude 2-[(E)-2-phenylethenyl]-5-(tetrahydro-2H-pyran-2-yloxy)-4-pyrimidinyl trifluoromethanesulfonate (6.8 mmol) was reacted with a 0.5M solution of ammonia in 1,4-dioxane (136 mL) in a pressure bottle at 60° C. for 24 h. The reaction was concentrated under vacuum, the residue was taken up in DCM and washed with water, saturated aq. NaHCO3, and brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by column chromatography (silica gel) using a MeOH/DCM gradient to yield the desired compound as a tan solid (1.28 g, 63% for two steps).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. washwashed with water, saturated aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d6f2c5f83940420eb99d883009534214
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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