Phosphate → HCID 86652263, compound

HRID 1409123Notes

Reaction equation

HRID 1409123 reaction equation
[Si]([O:8][CH2:9][C:10]([C:13]1[CH:32]=[CH:31][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([Cl:26])[N:23]3[N:27]=[C:28]([CH3:30])[CH:29]=[C:22]3[N:21]=2)=[O:18])=[CH:15][CH:14]=1)([CH3:12])[CH3:11])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].P([O-])([O-])([O-])=O>C1COCC1>[Cl:26][C:24]1[N:23]2[N:27]=[C:28]([CH3:30])[CH:29]=[C:22]2[N:21]=[C:20]([NH:19][C:17](=[O:18])[C:16]2[CH:31]=[CH:32][C:13]([C:10]([CH3:11])([CH3:12])[CH2:9][OH:8])=[CH:14][CH:15]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 2724141Tetrabutylammonium FluorideHCID 86652264HCID 86652264, compound

Product 1

HCID 86652263HCID 86652263, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (4F, 3.9 g, 1.0 equivalent) was dissolved in THF (0.13 M) and treated with TBAF (1.0 M in THF, 4.0 equivalents). After 60 hours, pH 7 phosphate buffer was added and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography (SiO2, gradient of 25 to 50% EtOAc/hexanes) to give N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (s, 6H), 2.44 (s, 3H), 3.46 (d, J=5.05 Hz, 2H), 4.76 (t, J=5.31 Hz, 1H), 6.45 (s, 1H), 7.52 (d, J=8.59 Hz, 2H), 7.99 (d, J=8.59 Hz, 2H), 8.06 (s, 1H), 11.30 (s, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, gradient of 25 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b62849c2e671424b917d819bc1e920f9
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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