Isoamyl Nitrite → HCID 25023743, compound

HRID 2262172Notes

Reaction equation

HRID 2262172 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[N:9]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:11]3[S:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:23].[N:24](OCCC(C)C)=O>C(Cl)(Cl)Cl.C(O)(=O)C>[NH:23]1[C:3]2[C:2](=[C:7]([C:8]3[N:9]=[C:10]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:11]4[S:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH:6]=[CH:5][CH:4]=2)[CH:1]=[N:24]1

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 67191519HCID 67191519, compound

Product 1

HCID 25023743HCID 25023743, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

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

Workup

  1. customThe mixture was then quenched with sodium bicarbonate solution
  2. extractionextracted in to chloroform
  3. customThe residue was purified

Sources & evidence

ORD record
ord-12b09e7480034fc1b0ccbfcc41ea502a
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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