5-(1-Methyl-1H-pyrazol-4-yl)-4-(4-morpholinyl)-7H-Pyrrolo[2,3-d]pyrimidine → HCID 72706903, compound

HRID 1750290Notes

Reaction equation

HRID 1750290 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:5]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][N:8](COCC[Si](C)(C)C)[C:6]=2[N:7]=1.CN1C=C(C2C3C(N4CCOCC4)=NC=NC=3NC=2)C=N1>>[CH3:1][C:2]1[N:3]=[C:4]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:5]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 727068375-(1-Methyl-1H-pyrazol-4-yl)-4-(4-morpholinyl)-7H-Pyrrolo[2,3-d]pyrimidineHCID 86706961HCID 86706961, compound

Product 1

HCID 72706903HCID 72706903, compound

Procedure

3-[2-Methyl-4-(morpholin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (C25) was converted to the product using the method described for synthesis of 5-(1-methyl-1H-pyrazol-4-yl)-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine (1) in Example 1. In this case, preparative HPLC purification was carried out using a Phenomenex Gemini C18 column, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 30% to 50% B. The product was obtained as a white solid. Yield: 17.3 mg, 54.2 μmol, 45% over 2 steps. LCMS m/z 320.1 [M+H+]. 1H NMR (400 MHz, CD3OD) δ 7.91-7.93 (m, 1H), 7.85-7.88 (m, 1H), 7.60-7.69 (m, 2H), 7.38 (s, 1H), 3.51-3.55 (m, 4H), 3.24-3.28 (m, 4H), 2.59 (s, 3H).

Workup

  1. customIn this case, preparative HPLC purification
  2. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-a6860327f50f441e8003b69a9848e4fc
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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