4-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine → HCID 86706937, compound

HRID 1750256Notes

Reaction equation

HRID 1750256 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1.BrC1C2C([N:30]3[CH2:35][CH2:34][CH2:33][C@H:32]([CH3:36])[CH2:31]3)=NC=NC=2N(S(C2C=CC(C)=CC=2)(=O)=O)C=1>>[I:11][C:10]1[C:3]2[C:2]([N:30]3[CH2:35][CH2:34][CH2:33][C@H:32]([CH3:36])[CH2:31]3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=1

Participants

3

Reactant 2

HCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 867069385-bromo-7-[(4-methylphenyl)sulfonyl]-4-[(3S)-3-methylpiperidin-1-yl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86706937HCID 86706937, compound

Procedure

4-Chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C1) was converted to the product using the method described for synthesis of 5-bromo-7-[(4-methylphenyl)sulfonyl]-4-[(3S)-3-methylpiperidin-1-yl]-7H-pyrrolo[2,3-d]pyrimidine (C15) in Example 7. Yield: 7.38 g, 15.6 mmol, 80%. LCMS m/z 473.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.34 (s, 1H), 5.55 (s, 2H), 4.06-4.17 (m, 2H), 3.50-3.57 (m, 2H), 2.91 (ddd, J=12.6, 11.5, 3.5 Hz, 1H), 2.58 (dd, J=12.6, 10.8 Hz, 1H), 1.95-2.07 (m, 1H), 1.76-1.95 (m, 3H), 1.11-1.23 (m, 1H), 0.96 (d, J=6.8 Hz, 3H), 0.88-0.94 (m, 2H), −0.04 (s, 9H).

Sources & evidence

ORD record
ord-e784b9cbe0754cbe8bf1637ea13467d5
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

Loading…