3-Hydroxy-5-chloropyridine → HCID 10030369, compound

HRID 750849Notes

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][CH:41]=[C:42]([Cl:44])[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][CH:41]=[C:42]([Cl:44])[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 5823053-Hydroxy-5-chloropyridine

HCID 69199205HCID 69199205, compound

HCID 178418339Butyllithium

Product 1

HCID 10030369HCID 10030369, compound

Procedure

2-Cyclobutylmethoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (the Mrf product from Example 83), (40 mg, 0.08 mmol) was reacted with 2 equivalents each of n-butyl lithium and 3-hydroxy-5-chloro-pyridine according to the procedure described in Reference Examples 6 and 7 to afford 2-cyclobutylmethoxy-4-(5-chloro-3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: HPLC/MS: m/e=546 (M++1); Rt=5.20 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), 7.10-7.18 (m, 3H), 7.20-7.28 (m, 3H), 7.35 (d, J=2 Hz, 1H), 7.63 (m, 1H), 8.05 (d, J=2 Hz, 1H), 8.10 (d, J=2 Hz, 1H).

Sources & evidence

ORD record: ord-f4cbf081fcfa40648d909840fc8c364d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

Loading…