3-[6-Methyl-4-(4-morpholinyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile → HCID 86706940, compound

HRID 1750258Notes

Reaction equation

HRID 1750258 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:9][N:8](COCC[Si](C)(C)C)[C:4]=2[N:5]=[CH:6][N:7]=1.CC1NC2N=CN=C(N3CCOCC3)C=2C=1C1C=C(C=CC=1)C#N>>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 727068383-[6-Methyl-4-(4-morpholinyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrileHCID 86706939HCID 86706939, compound

Product 1

HCID 86706940HCID 86706940, compound

Procedure

4-Chloro-5-(1-methyl-1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C2) was converted to the product using the method described for synthesis of 3-[6-methyl-4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (2) in Example 2. In this case the product, obtained as a yellow solid, was purified by recrystallization from ethyl acetate, rather than via preparative HPLC. Yield: 1.0 g, 4.3 mmol, 43% over two steps. LCMS m/z 234.0 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 12.66 (brs, 1H), 8.58 (s, 1H), 7.91 (s, 1H), 7.69 (d, J=2.5 Hz, 1H), 7.63 (d, J=0.7 Hz, 1H), 3.89 (s, 3H).

Workup

  1. customIn this case the product, obtained as a yellow solid
  2. customwas purified by recrystallization from ethyl acetate, rather than via preparative HPLC

Sources & evidence

ORD record
ord-78e2fe29c69f4e0ebbd07fdd05bf3047
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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