Water → HCID 86686234, compound

HRID 1021283Notes

Reaction equation

HRID 1021283 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][Si](C(C)(C)C)(C)C)[C:20]=3[F:34])[CH2:15][CH2:14]2)=[CH:9][N:8]=1)(=O)=O.C1COCC1.[CH3:42][O:43][CH2:44][CH2:45][NH2:46].O>CCOC(C)=O>[F:34][C:20]1[C:19]([N:16]2[CH2:17][CH2:18][N:13]([C:10]3[CH:9]=[N:8][C:7]([NH:46][CH2:45][CH2:44][O:43][CH3:42])=[N:12][CH:11]=3)[CH2:14][CH2:15]2)=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:25][OH:26]

Participants

6

Reactant 4

HCID 962WaterHCID 80182-MethoxyethylamineHCID 8028TetrahydrofuranHCID 86686235HCID 86686235, compound

Product 1

HCID 86686234HCID 86686234, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5-{4-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperazin-1-yl}pyrimidin-2-yl trifluoromethanesulfonate (200 mg) was mixed with THF (4 ml), and 2-methoxyethanamine (864 mg) was added thereto, followed by stirring at 60° C. overnight. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. The obtained residue was mixed with THF (5 ml), and a 1 M TBAF/THF solution (1.6 ml) was added thereto, followed by stirring at room temperature overnight. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain [2-fluoro-3-(4-{2-[(2-methoxyethyl)amino]pyrimidin-5-yl}piperazin-1-yl)phenyl]methanol (105 mg).

Workup

  1. additionwas added
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. additionThe obtained residue was mixed with THF (5 ml)
  4. additiona 1 M TBAF/THF solution (1.6 ml) was added
  5. stirringby stirring at room temperature overnight
  6. additionWater and EtOAc were added to the reaction mixture
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-04d257c4068b4514913bad00e4cace84
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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