N-bromobutanimide → HCID 86717534, compound

HRID 712076Notes

Reaction equation

HRID 712076 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[N:4]([CH:5]=[N:6][C:7]3[CH:13]=[CH:12][S:11][C:8]=32)[N:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)Cl>[Br:14][C:10]1[C:2]([CH3:1])=[N:3][N:4]2[C:9]=1[C:8]1[S:11][CH:12]=[CH:13][C:7]=1[N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86717533HCID 86717533, compound

Product 1

HCID 86717534HCID 86717534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-methylpyrazolo[1,5-c]thieno[2,3-e]pyrimidine (1.01 g, 5.34 mmol) in methylene chloride (30 mL) was added N-bromosuccinimide (0.959 g, 5.39 mmol). After stirring for 1 h, the reaction solution was concentrated, and the resultant residue was purified with flash chromatography (eluting with a gradient of 0-20% ethyl acetate in hexanes) to give the desired product as whited solid. 1H NMR (300 MHz, CD3OD) δ 9.11 (1H, s), 7.94 (1H, d, J=5.3 Hz), 7.52 (1H, d, J=5.3 Hz), 2.48 (3H, s) ppm. LCMS calculated for C9H7BrN3S (M+H)+: m/z=268.0. Found: 267.9.

Workup

  1. concentrationthe reaction solution was concentrated
  2. customthe resultant residue was purified with flash chromatography (
  3. washeluting with a gradient of 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-55448f7c17a343158dbcd8e736073fa2
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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