Potassium Carbonate → 4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine, formate salt

HRID 1750285Notes

Reaction equation

HRID 1750285 reaction equation
[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:17]=[N:18][NH:19][CH:20]=4)=[CH:14][N:13](CO)[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:23](=O)([O-:25])[O-:24].[K+].[K+]>C(#N)C>[CH:23]([OH:25])=[O:24].[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:20]=[N:19][NH:18][CH:17]=4)=[CH:14][NH:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86706958[4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol

Product 1

HCID 1317336074-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine, formate salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of [4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol (C21) (from the previous step, 0.10 g, ≦0.32 mmol) in acetonitrile (10 mL) was added potassium carbonate (0.34 g, 2.5 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filter cake was washed with ethyl acetate (3×20 mL). The combined filtrates were concentrated in vacuo; purification via preparative HPLC (Column: DIKMA Diamonsil(2) C18, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Gradient: 0% to 17% B) afforded the product as a pale solid. Yield: 36 mg, 0.11 mmol, 34% over 2 steps. LCMS m/z 271.2 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 10.72 (brs, 1H), 8.47 (s, 1H), 7.78 (s, 2H), 7.19 (s, 1H), 3.60-3.67 (m, 4H), 3.41-3.48 (m, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethyl acetate (3×20 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. custompurification via preparative HPLC (Column: DIKMA Diamonsil(2) C18, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Gradient: 0% to 17% B)

Sources & evidence

ORD record
ord-92ae983ec0e94edcab4dd4d9835f0f19
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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