Potassium Carbonate → 3-[6-Methyl-4-(4-morpholinyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile

HRID 1750267Notes

Reaction equation

HRID 1750267 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[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[C:21]#[N:22])=[C:4]1[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:26][C:4]1[NH:3][C:7]2[N:8]=[CH:9][N:10]=[C:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[C:6]=2[C:5]=1[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86706948HCID 86706948, compound

Product 1

HCID 727068383-[6-Methyl-4-(4-morpholinyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[7-(hydroxymethyl)-6-methyl-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (C9) (from the previous step, 125 mg, ≦0.278 mmol) in acetonitrile (5 mL) was adjusted to a pH of >11 by addition of solid potassium carbonate. The mixture was filtered and concentrated in vacuo; purification via preparative HPLC (Column: Boston Symmetrix ODS-H, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Gradient: 19% to 39% B) afforded the product as a yellow solid. Yield: 54 mg, 0.17 mmol, 61% over two steps. LCMS m/z 319.9 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 12.17 (br s, 1H), 8.34 (s, 1H), 7.77-7.83 (m, 2H), 7.65-7.74 (m, 2H), 3.27-3.33 (m, 4H), 2.98-3.06 (m, 4H), 2.36 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. custompurification via preparative HPLC (Column: Boston Symmetrix ODS-H, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Gradient: 19% to 39% B)

Sources & evidence

ORD record
ord-4c5d00a3f08444b8b24a3e3060b86d35
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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