6-Fluoropyridin-3-ol → HCID 10256470, compound

HRID 750848Notes

Reaction equation

[CH:1]1([CH2:5][O:6][C:7]2[N:12]=[C:11](S(C)(=O)=O)[C:10]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:8]=2)[CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[OH:37][C:38]1[CH:39]=[N:40][C:41]([F:44])=[CH:42][CH:43]=1>>[CH:1]1([CH2:5][O:6][C:7]2[N:12]=[C:11]([O:37][C:38]3[CH:39]=[N:40][C:41]([F:44])=[CH:42][CH:43]=3)[C:10]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:8]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 27631086-Fluoropyridin-3-ol

HCID 69199205HCID 69199205, compound

HCID 178418339Butyllithium

Product 1

HCID 10256470HCID 10256470, compound

Procedure

2-Cyclobutylmethoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (the MRf product from Example 83), (30 mg, 0.06 mmol) was reacted with 2 equivalents each of n-butyl lithium and 3-hydroxy-6-fluoro-pyridine according to the procedure described in Reference Examples 6 and 7 to afford 2-cyclobutylmethoxy-4-(6-fluoro-3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: HPLC/MS: m/e=530 (M++1); Rt=5.01 min. 1H-NMR 400 MHz (CDCl3): δ 1.80-1.98 (m, 4H), 2.10-2.11(m, 2H), 2.74 (m, 1H), 4.20 (d, J=7 Hz, 2H), 7.00 (m, 1H), 7.13-7.18 (m, 2H), 7.20-7.30 (m, 5H), 7.63-7.68 (m, 1H), 8.11 (m, 1H).

Sources & evidence

ORD record: ord-a137a97419924986836cf8a3f952b2d9
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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