Hydrochloric Acid → 1-[4-(4-Oxazolo[5,4-b]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethanol

HRID 394508Notes

Reaction equation

HRID 394508 reaction equation
C([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[O:22][C:23]4[C:28]([N:29]=3)=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:17][CH2:16]2)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=O)CCC.Cl.[OH-].[Na+]>O1CCOCC1>[N:29]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[O:22][C:21]=1[N:18]1[CH2:17][CH2:16][N:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([C@H:7]([OH:6])[CH3:8])[N:14]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11143754(R)-1-[4-(4-Oxazolo[5,4-b]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate

Product 1

HCID 108819401-[4-(4-Oxazolo[5,4-b]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethanolYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-1-[4-(4-oxazolo[5,4-b]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate (prepared according to the method of Example 9, Step B, 11.0 g, 27.6 mmol) in dioxane (11.5 mL) was added concentrated hydrochloric acid (23 mL, 276 mmol). This mixture was stirred at room temperature overnight, neutralized with 6 N aqueous sodium hydroxide, and extracted with chloroform (3×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (3.5% methanol/chloroform) to give 8.4 g (93%) of the title compound as a white solid. mp: 153-156° C.; 1H NMR (CDCl3, 300 MHz) δ 8.25 (d, 1H), 7.95 (dd, 1H), 7.58 (dd, 1H), 7.15 (dd, 1H), 6.45 (d, 1H), 4.72 (q, 1H), 4.25 (brs, 1H), 3.85-3.82 (c, 8H), 1.51 (d, 3H); MS (Cl/NH3) 327 (MH+); [α]D+16.1 (c 1.0, MeOH).

Workup

  1. extractionextracted with chloroform (3×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by flash column chromatography (3.5% methanol/chloroform)

Sources & evidence

ORD record
ord-ec5ccc320bb04c4d98e1085ce958b94a
Source dataset
uspto-grants-2003_08
Patent number
US06602875B2

Reaction notes

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