3-Hydroxypyridine → HCID 10390632, compound

HRID 750826Notes

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.C([Li])CCC.[OH:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1>>[CH:1]1([O:4][C:5]2[N:10]=[C:9]([O:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=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

Reactant 3

HCID 79713-Hydroxypyridine

HCID 69199118HCID 69199118, compound

HCID 178418339Butyllithium

Product 1

HCID 10390632HCID 10390632, compound

Procedure

2-Cyclopropyloxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Middle Rf product) (Example 55, Step A), (28 mg, 0.06 mmol) was reacted with 1 equivalent each of n-butyl lithium and 3-hydroxypyridine by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 80/20 hexanes/ethyl acetate) afforded the title compound. HPLC/MS: m/e=498 (M+−1); Rt=4.30 min. 1H-NMR 500 MHz (CDCl3): δ 0.30 (m, 2H), 0.59 (m, 2H), 1.26 (m, J=5 Hz, 1H), 4.09 (s, 2H), 7.18-7.30 (m, 6H), 7.36 (d, J=2 Hz, 1H), 7.40 (dd, J=7 Hz, J=5 Hz, 1H), 7.57 (d, J=7 Hz, 1H), 8.53 (d, J=5 Hz, 2H).

Sources & evidence

ORD record: ord-9e86cefabeb942d7a78c00ef4542249a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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