Potassium Carbonate → 5-(1-Methyl-1H-pyrazol-4-yl)-4-(4-morpholinyl)-7H-Pyrrolo[2,3-d]pyrimidine

HRID 1750262Notes

Reaction equation

HRID 1750262 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[N:13][CH:12]=[N:11][C:10]=3[N:9](CO)[CH:8]=2)[CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[N:13][CH:12]=[N:11][C:10]=3[NH:9][CH:8]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86706944HCID 86706944, compound

Product 1

HCID 727068375-(1-Methyl-1H-pyrazol-4-yl)-4-(4-morpholinyl)-7H-Pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [5-(1-methyl-1H-pyrazol-4-yl)-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol (C5) (material from the previous step, ≦0.48 mmol) in methanol (5 mL) was brought to a pH of >12 via addition of solid potassium carbonate. The reaction mixture was stirred for 30 minutes, filtered, and concentrated in vacuo. Purification via preparative HPLC (Column: Agella Venusil ASB C18, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Eluent: 13% B) provided the product as a yellow solid. Yield over two steps: 90 mg, 0.32 mmol, 67%. LCMS m/z 285.1 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 12.96 (br s, 1H), 8.47 (s, 1H), 7.85 (s, 1H), 7.57 (s, 1H), 7.52 (d, J=2.5 Hz, 1H), 3.90 (s, 3H), 3.53-3.59 (m, 4H), 3.45-3.51 (m, 4H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification via preparative HPLC (Column: Agella Venusil ASB C18, 5 μm; Mobile phase A: 0.225% formic acid in water; Mobile phase B: acetonitrile; Eluent: 13% B)

Sources & evidence

ORD record
ord-e85396e29eba433990af3542db3b9099
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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