3-Hydroxypyridine → HCID 10074610, compound

HRID 750869Notes

Reaction equation

HRID 750869 reaction equation
[N:1]1([C:6]2[N:11]=[C:10](S(C)(=O)=O)[C:9]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C1N=C(N2CCCC2)C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2Cl)N=1)(=O)=O.C([Li])CCC.[OH:66][C:67]1[CH:68]=[N:69][CH:70]=[CH:71][CH:72]=1>>[N:1]1([C:6]2[N:11]=[C:10]([O:66][C:67]3[CH:68]=[N:69][CH:70]=[CH:71][CH:72]=3)[C:9]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 79713-HydroxypyridineHCID 69197659HCID 69197659, compoundHCID 69200309HCID 69200309, compoundHCID 178418339Butyllithium

Product 1

HCID 10074610HCID 10074610, compound

Procedure

2-(N-pyrrolidinyl)-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (HRf product from Example 36, Step A (50 mg, 0.10 mmol) was reacted with 2 equivalents each of n-butyl lithium and 3-hydroxypyridine by the procedure described in Reference Example 6 and 7 to afford the title compound: HPLC/MS: m/e=497 (M++1); Rt=3.84 min. 1H-NMR 400 MHz (CDCl3): δ 1.91-2.00 (m, 4H), 3.23-3.35 (s, 2H), 3.55-3.62 (s, 2H), 7.08-7.21 (m, 6H), 7.35-7.39 (m, 2H), 7.56-7.58 (m, 1H), 8.48 (d, J=6 Hz, 1H), 8.58 (s, 1H).

Sources & evidence

ORD record
ord-2cdafb30bcea4817abd810cba0c65e72
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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