Pyrrolidine → HCID 10325170, compound

HRID 750816Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)(=O)=O.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[N:36]1([C:5]2[N:10]=[C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=3)[C:8]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[C:7]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[N:6]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 59753934HCID 59753934, compound

Product 1

HCID 10325170HCID 10325170, compound

Procedure

2-(Methylsulfonyl)-4-(3,4-difluorobenzyloxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 6, 55 mg, 0.10 mmol) was reacted in excess neat pyrrolidine at 80° C. overnight by the general procedure described in Example 31, Step A. Workup (solvent removal under reduced pressure) and flash column chromatography on silica gel (eluted with 92/8 hexanes/ethyl acetate) afforded the title compound. HPLC/MS: m/e=548 (M++1); Rt=4.76 min. 1H-NMR 500 MHz (CDCl3): δ 2.02 (bs, J=4H), 3.63 (bs, 4H), 5.40 (s, 2H), 7.04 (d, J=8 Hz, 2H), 7.08-7.20 (m, 7H), 7.34 (d, J=2 Hz, 1H).

Workup

customWorkup (solvent removal under reduced pressure) and flash column chromatography on silica gel (eluted with 92/8 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-c892ea769a48448bbef1ad44b4af9721
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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