Phosphate → HCID 86652263, compound

HRID 1256282Notes

Reaction equation

HRID 1256282 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, 6 H), 2.44 (s, 3 H), 3.46 (d, J=5.05 Hz, 2 H), 4.76 (t, J=5.31 Hz, 1 H), 6.45 (s, 1 H), 7.52 (d, J=8.59 Hz, 2 H), 7.99 (d, J=8.59 Hz, 2 H), 8.06 (s, 1 H), 11.30 (s, 1 H).

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-d73906e372e44abeb342a73fa55f4c91
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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