Potassium Carbonate → HCID 72706839, compound

HRID 1750270Notes

Reaction equation

HRID 1750270 reaction equation
OC[N:3]1[C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:6]=2[C:5]([C:18]2[N:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][CH:19]=2)=[CH:4]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:12]1([C:11]2[C:6]3[C:5]([C:18]4[N:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][CH:19]=4)=[CH:4][NH:3][C:7]=3[N:8]=[CH:9][N:10]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 867069506-[7-(hydroxymethyl)-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-2-carbonitrile

Product 1

HCID 72706839HCID 72706839, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-[7-(hydroxymethyl)-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-2-carbonitrile (C11) (from the previous step, 85 mg, ≦0.25 mmol) in acetonitrile (3 mL) was brought to a pH of >12 via addition of solid potassium carbonate. After 30 minutes at room temperature, the reaction mixture was filtered and concentrated in vacuo. Purification via preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 10% to 50% B) afforded the product as a white solid. Yield: 15.2 mg, 49.6 μmol, 20% over two steps. LCMS m/z 307.2 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.13 (dd, J=8.1, 7.7 Hz, 1H), 7.96 (br d, J=8 Hz, 1H), 7.89 (br d, J=8 Hz, 1H), 7.86 (s, 1H), 3.50-3.55 (m, 4H), 3.19-3.24 (m, 4H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customPurification via preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 10% to 50% B)

Sources & evidence

ORD record
ord-fcd29748145c49d791ff661db3fdae68
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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