3-{4-[(2S)-2-Methylmorpholin-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}benzonitrile → HCID 86706960, compound

HRID 1750288Notes

Reaction equation

HRID 1750288 reaction equation
Cl[C:2]1[C:3]2[C:11]([I:12])=[CH:10][N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.C[C@@H:22]1[O:27][CH2:26][CH2:25][N:24](C2C3C(C4C=C(C=CC=4)C#N)=CNC=3N=CN=2)[CH2:23]1>>[I:12][C:11]1[C:3]2[C:2]([N:24]3[CH2:25][CH2:26][O:27][CH2:22][CH2:23]3)=[N:7][C:6]([CH3:8])=[N:5][C:4]=2[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=1

Participants

3

Reactant 2

HCID 727069043-{4-[(2S)-2-Methylmorpholin-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}benzonitrileHCID 86706959HCID 86706959, compound

Product 1

HCID 86706960HCID 86706960, compound

Procedure

The product was prepared from 4-chloro-5-iodo-2-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C23) according to the method described for synthesis of 3-{4-[(2S)-2-methylmorpholin-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}benzonitrile (6) in Example 6. In this case, purification was carried out via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in petroleum ether) to provide the product as a yellow oil. Yield: 300 mg, 0.63 mmol, 67%. LCMS m/z 475.2 [M+H+].

Workup

  1. customIn this case, purification

Sources & evidence

ORD record
ord-aa491738ce4947cf9bb2925a4457d7bc
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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