PF-06447475 → HCID 86706971, compound

HRID 1750300Notes

Reaction equation

HRID 1750300 reaction equation
[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=4)[C:19]#[N:20])=[CH:14][NH:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.ClC1C2C(I)=CN([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])C=2N=CN=1>>[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=4)[C:19]#[N:20])=[CH:14][N:13]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 72706840PF-06447475HCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86706971HCID 86706971, compound

Procedure

3-[4-(Morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (4) was converted to the product using the method described for synthesis of 4-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C1) in Preparation P1. The product was obtained as a yellow solid. Yield: 0.90 g, 2.1 mmol, 70%. 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 7.86 (br s, 1H), 7.79 (br d, J=7.6 Hz, 1H), 7.63 (br d, J=7.6 Hz, 1H), 7.57 (dd, J=7.6, 7.6 Hz, 1H), 7.29 (s, 1H), 5.67 (s, 2H), 3.58-3.64 (m, 2H), 3.52-3.58 (m, 4H), 3.27-3.32 (m, 4H), 0.92-0.98 (m, 2H), −0.03 (s, 9H).

Workup

  1. customThe product was obtained as a yellow solid

Sources & evidence

ORD record
ord-bcb4d90a068b44d2a390265e803dd3e8
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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