Pyrrolidine → 2-(2-Pyrrolidinyl)-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750871Notes

Reaction equation

HRID 750871 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=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.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1>[NH:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=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

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 104138842-Methylsulfonyl-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Product 1

HCID 99833562-(2-Pyrrolidinyl)-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylsulfonyl-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 109 (45 mg, 0.09 mmol) was reacted with excess pyrrolidine (0.5 mL) in THF at a sealed tube 60° C. for overnight by general procedure Example 103 to afford the title compound: HPLC/MS: m/e=497 (M++1); Rt4.21 min. 1H-NMR 400 MHz (CDCl3): δ 1.85-1.95 (s 4H), 3.20-3.60 (m, 4H), 7.00-7.19 (m, 8H), 7.31 (d, J=2 Hz, 1H), 7.75-7.80 (m, 1H), 8.38 (m, 1H).

Sources & evidence

ORD record
ord-2592b8ace6f94042847e905f12991664
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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