2-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine → HCID 67191519, compound
Reaction equation
[CH3:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:17].Cl[C:19]1[N:20]=[C:21]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:22]2[S:27][CH:26]=[CH:25][C:23]=2[N:24]=1>>[CH3:1][C:2]1[C:7]([C:19]2[N:20]=[C:21]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:22]3[S:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:17]Participants
3
Procedure
Reaction of 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine with 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine under Suzuki conditions yielded 2-methyl-3-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine. To a solution of 2-methyl-3-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine (80 mg) in chloroform (8 mL) and acetic acid (4 mL) was added isoamyl nitrite (36 μL). The reaction mixture was stirred for 1 day at room temperature. The mixture was then quenched with sodium bicarbonate solution and extracted in to chloroform and reduced in vacuo. The residue was purified using flash chromatography to yield 270. MS: ESI MH+ 338
Sources & evidence
- ORD record
- ord-acb2606a8ed64a26aab637a48332fbfb
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846929B2
Reaction notes
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