Sodium hydride → 2-[2-(3-Fluoropropoxy)pyrimidine-4-yl]-6-methoxybenzothiophene

HRID 454811Notes

Reaction equation

HRID 454811 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:12]=[CH:11][N:10]=1>>[F:1][CH2:2][CH2:3][CH2:4][O:5][C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 680423-Fluoro-1-propanolHCID 866465552-(2-Chloropyrimidine-4-yl)-6-methoxybenzothiophene

Product 1

HCID 469475472-[2-(3-Fluoropropoxy)pyrimidine-4-yl]-6-methoxybenzothiopheneYield 65.4%

Procedure

2-[2-(3-Fluoropropoxy)pyrimidine-4-yl]-6-methoxybenzothiophene (1-32, 75 mg, 65%) was prepared in the same manner as in Example 31 as a pale yellow solid using 3-fluoro-1-propanol (40 mL, 0.54 mmol), sodium hydride (NaH, 22 mg, 0.54 mmol) and 2-(2-chloropyrimidine-4-yl)-6-methoxybenzothiophene (105a, 100 mg, 0.36 mmol) obtained in Preparation Example 19.

Workup

  1. customobtained in Preparation Example 19

Sources & evidence

ORD record
ord-7174684f3c7f4527b7c6cfe771d1f13c
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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