Potassium Carbonate → 1-[4-(4-Oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethanol

HRID 394506Notes

Reaction equation

HRID 394506 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[CH:24]=[N:25][CH:26]=[CH:27][C:28]=4[N:29]=3)[CH2:17][CH2:16]2)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=O)CCC.C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[NH4+]>[N:29]1[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=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 2

HCID 11430Potassium CarbonateHCID 11133045(R)-1-[4-(4-Oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate

Product 1

HCID 109583501-[4-(4-Oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethanolYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (R)-1-[4-(4-oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate (prepared according to the method of Example 2, Step A, 1.2 g, 3.0 mmol) in methanol (30 mL) was added potassium carbonate (823 mg, 6.0 mmol). This mixture was stirred at room temperature for 5 h, diluted with saturated aqueous ammonium chloride, concentrated, and extracted with chloroform (3×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (6% methanol/chloroform) to give 915 mg (94%) of the title compound as a white solid after tritration with hexanes. mp: 181-183° C.; 1H NMR (CDCl3, 300 MHz) δ 8.54 (d, 1H), 8.35 (d, 1H), 8.25 (d, 1H), 7.27 (dd, 1H), 6.44 (d, 1H), 4.71 (q, 1H), 4.25 (br s, 1H), 3.86-3.83 (c, 8H), 1.50 (d, 3H); MS (APCI) 327 (MH+); [α]D+15.3 (c 0.5, MeOH).

Workup

  1. concentrationconcentrated
  2. extractionextracted with chloroform (3×)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash column chromatography (6% methanol/chloroform)

Sources & evidence

ORD record
ord-27c844134f9543dcb4c87f0d58c4b189
Source dataset
uspto-grants-2003_08
Patent number
US06602875B2

Reaction notes

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