1-Pentanol → HCID 59753897, compound

HRID 750859Notes

Reaction equation

HRID 750859 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:6]=1)(=O)=O.C([Li])CCC.[CH2:38]([OH:43])[CH2:39][CH2:40][CH2:41][CH3:42]>>[CH2:38]([O:43][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:6]=1)[CH2:39][CH2:40][CH2:41][CH3:42]

Participants

4

Reactant 3

HCID 62761-PentanolHCID 10255652HCID 10255652, compoundHCID 178418339Butyllithium

Product 1

HCID 59753897HCID 59753897, compound

Procedure

2-Methylsulfonyl-4-(3-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 86 (30 mg, 0.06 mmol) was reacted with 2 equivalents each of n-butyl lithium and n-pentanol by the procedure described in Reference Examples 6 and 7 to afford the title compound: HPLC/MS: m/e=514 (M++1); Rt'4.48 min. 1H-NMR 400 MHz (CDCl3): δ 0.89-0.91 (t, 3H), 1.26-1.40 (m, 4H), 1.69-1.76 (m, 2H), 4.19-4.22 (t, 2H), 7.15-7.28 (m, 6H), 7.35 (d, J=2 Hz, 1H), 7.40-7.43 (m, 1H), 7.58-7.61 (m, 1H), 8.52-8.55 (m, 2H).

Sources & evidence

ORD record
ord-e4b6f175586544e19a19b15cbcff5fd9
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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