Isoamyl Nitrite → 2-(1H-indazol-6-yl)-4-morpholinothieno[3,2-d]pyrimidine

HRID 2098720Notes

Reaction equation

HRID 2098720 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([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: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](=[CH:7][CH:6]=[C:5]([C:8]3[N:9]=[C:10]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[C:11]4[S:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH:4]=2)[CH:1]=[N:24]1

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 671889492-Methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine

Product 1

HCID 250237442-(1H-indazol-6-yl)-4-morpholinothieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine (99 mg) in chloroform (10 mL) and acetic acid (2 mL) was added isoamyl nitrite (44 μL). The reaction mixture was stirred for 2 days 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 229. 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-7612dd26b14a4bc7a35bcbf943d46688
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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