Pyrrolidine → HCID 10482582, compound

HRID 750876Notes

Reaction equation

HRID 750876 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][O:6][C:7]1[N:12]=[C:11](S(C)(=O)=O)[C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[N:8]=1.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][O:6][C:7]1[N:12]=[C:11]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[N:8]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 59753907HCID 59753907, compound

Product 1

HCID 10482582HCID 10482582, compound

Procedure

2-(3,4-Difluorobenzyloxy)-4-(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-pyrimidine (Reference Example 7) (30 mg, 0.05 mmol) was reacted with pyrrolidine (37.7 mg, 0.53 mmol) by the same general procedure described in Example 103 to afford the title compound after flash column chromatography on silica gel (eluted with 90/10 hexanes/ethyl acetate): HPLC/MS: m/e=546 (M++1); Rt=3.70 min. 1H-NMR 400 MHz (CDCl3): δ 1.75-1.80 (br, 4H), 3.10-3.20 (br, 4H), 5.32-5.42 (m, 2H), 6.95 (d, J=9 Hz, 1H), 7.05-7.21 (m, 8H), 7.35-7.40 (m, 1H).

Sources & evidence

ORD record
ord-8dc124514f334c20be1658045e754a52
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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