Chlorotrimethylsilane → 3-Methoxy-4-[4-(4-nitro-phenoxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-benzoic acid benzyl ester

HRID 1427380Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[C:5]([C:18]([F:21])([F:20])[F:19])=[CH:4][N:3]=1.[CH2:22]([O:29][C:30](=[O:40])[C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[C:33]([O:38][CH3:39])[CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C[Si](Cl)(C)C>CC(O)C>[CH2:22]([O:29][C:30](=[O:40])[C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)[C:5]([C:18]([F:21])([F:20])[F:19])=[CH:4][N:3]=2)=[C:33]([O:38][CH3:39])[CH:32]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

b-3.) 1.0 g of 2-chloro-4-(4-nitrophenyloxy)-5-trifluoromethylpyrimidine and 0.77 g of 4-amino-3-methoxy-benzoic acid benzyl ester are suspended in 15 mL of 2-propanol. The suspension is heated to 50° C. and 0.08 mL trimethylsilylchloride (TMSCl) are added. The suspension is stirred for 16 hours at 50° C. The suspension is cooled to ambient temperature and stirred for 3 hours. The precipitate is filtered and washed with 2-propanol. After drying in a vacuum drying oven 1.38 g (85% of theory) of the corresponding 2-amino pyrimidine derivative product, i.e. 3-methoxy-4-[4-(4-nitro-phenoxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-benzoic acid benzyl ester is obtained.

Workup

temperatureThe suspension is cooled to ambient temperature
stirringstirred for 3 hours
filtrationThe precipitate is filtered
washwashed with 2-propanol
customAfter drying in a vacuum
dry with materialdrying oven 1.38 g (85% of theory) of the corresponding 2-amino pyrimidine derivative product

Sources & evidence

ORD record: ord-34bc391237924626a6880eb9b9d72502
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933227B2

Reaction notes

Loading…