Sodium hydride → HCID 11755101, compound

HRID 750860Notes

Reaction equation

HRID 750860 reaction equation
[CH:1]1([O:4][C:5]2[N:10]=[C:9](S(C)(=O)=O)[C:8]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:7]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:6]=2)[CH2:3][CH2:2]1.[H-].[Na+].[OH:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>>[CH:1]1([O:4][C:5]2[N:10]=[C:9]([O:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[C:8]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:7]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 69199118HCID 69199118, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 11755101HCID 11755101, compound

Procedure

2-Cyclopropyloxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (MRf product) (Example 55, Step A), (25 mg, 0.05 mmol) was reacted with 1.1 equivalents each of sodium hydride (60% in oil, 2.5 mg, 0.06 mmol) and 4-hydroxypyridine (5.9 mg, 0.062 mmol) by the procedure described in Examples 16 to afford the title compound: HPLC/MS: m/e=498 (M++1); Rt=3.49 min. 1H-NMR 400 MHz (CDCl3): δ 1.60-1.90 (m, 4H), 2.74 (m, 1H), 4.12 (d, J=7 Hz, 2H), 7.10-7.18 (m, 3H), 7.20-7.30 (m, 5H), 7.35 (d, J=2 Hz, 1H), 8.66 (d, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-414dbbd511fe415d8bc573913a53c223
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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