5-Hexyn-1-ol → 6-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-hex-5-yn-1-ol

HRID 417843Notes

Reaction equation

HRID 417843 reaction equation
[Cl:1][C:2]1[C:3]2[C:11](I)=[CH:10][N:9]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[CH2:24]([OH:30])[CH2:25][CH2:26][CH2:27][C:28]#[CH:29]>>[NH2:8][C:6]1[N:7]=[C:2]([Cl:1])[C:3]2[C:11]([C:29]#[C:28][CH2:27][CH2:26][CH2:25][CH2:24][OH:30])=[CH:10][N:9]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[C:4]=2[N:5]=1

Participants

3

Reactant 2

HCID 702345-Hexyn-1-olHCID 442289644-Chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 119510656-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-hex-5-yn-1-ol

Procedure

The title compound was prepared by Sonogashira coupling of 4-chloro-5-iodo-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (see Example 1) with 5-hexyn-1-ol according to the General Procedure A. tR: 4.92 min. 1H-NMR (DMSO-d6) δ 8.04 (s, 1H), 7.22 (s, 1H), 6.69 (br. s, 2H), 5.25 (s, 2H), 4.39 (t, 1H), 3.70 (s, 3H), 3.40 (q, 2H), 2.39 (t, 2H), 2.23 (s, 3H), 2.14 (s, 3H), 1.55 (m, 4H).

Sources & evidence

ORD record
ord-62e1377b48734fe8b60e461cd4831364
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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