Tetrabutylammonium Fluoride → HCID 58777630, compound

HRID 1371735Notes

Reaction equation

HRID 1371735 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([F:16])=[C:14]([F:17])[CH:13]=[C:12]([O:18][Si](C(C)(C)C)(C)C)[C:11]=2[O:26][CH3:27])=[O:9])=[CH:6][N:5]=[C:4]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:11]([O:26][CH3:27])=[C:12]([OH:18])[CH:13]=[C:14]([F:17])[C:15]=2[F:16])=[O:9])=[CH:6][N:5]=[C:4]([NH:28][CH:29]2[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:36])=[O:37])[CH2:33][CH2:34]2)[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58777580HCID 58777580, compound

Product 1

HCID 58777630HCID 58777630, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-[3-(tert-butyl-dimethyl-silanyloxy)-5,6-difluoro-2-methoxy-phenyl]-methanone (675 mg, 1.181 mmol, Example 270) in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (1.240 mL, 1.24 mmol, 1 M solution in tetrahydrofuran, Aldrich). The mixture was stirred at room temperature for 15 minutes and then concentrated to dryness. The residue was taken up in methylene chloride and washed with saturated solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solids were filtered off and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, 60 Å silica gel, eluting with 65–80% ethyl acetate in hexanes then 5% methanol in ethyl acetate) yielded [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5-hydroxy-6-methoxy-phenyl)-methanone as white solids (315 mg, 58%). HR-MS (ES, m/z) calculated for C18H22N5O5SF2 [(M+H)+] 458.1308, observed 458.1304.

Workup

  1. concentrationconcentrated to dryness
  2. washwashed with saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography (Biotage system, 60 Å silica gel
  7. washeluting with 65–80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-771e8d52dac54b74a6770cc7a95b53c5
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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