Benzenemethanamine, 3-chloro- → HCID 59753899, compound

HRID 750800Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:7][N:6]=1)(=O)=O.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31]>CN(C=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH:31][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:7][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 5 mL round bottom flask fitted with a stirrer bar and rubber septum was added 1 mL DMF and 2-methylsulfonyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (103 mg, 0.2 mmol) from Step A. Then 3-chlorobenzyl amine (2 eq, 50 μL, 0.4 mmol) was added vial syringe and the mixture heated at 100° C. for 4 h. HPLC/MS, showed that the starting material had been converted to the desired product. The product was extracted from 10 mL water with 20 mL ether, dried over MgSO4, filtered and the solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 92/8 hexanes/ethyl acetate) afforded the desired product. HPLC/MS: m/e=476 (M+1); Rt=4.70 min; 1H-NMR 500 MHz (CDCl3): δ 5.46 (s, 2H), 7.08 (d, J=9 Hz, 2H), 7.31-7.4 (m, 5H), 7.41-7.53 (m, 4H), 9.00 (s, 1H).

Workup

customTo a 5 mL round bottom flask fitted with a stirrer bar

Sources & evidence

ORD record: ord-be0142833f1e4f34b85135542a8501bc
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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