1-Methylpiperazine → 6-[(4-Methylpiperazin-1-yl)methyl]-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 227607Notes

Reaction equation

HRID 227607 reaction equation
Br[CH2:2][C:3]1[S:12][C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=2[C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:2][C:3]2[S:12][C:6]3[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=3[C:4]=2[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 590995626-(Bromomethyl)-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 116251676-[(4-Methylpiperazin-1-yl)methyl]-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amineYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 57A (330 mg) and N-methylpiperazine (0.3 mL, 2.71 mmol) in DMF (6 mL) was stirred at room temperature overnight and concentrated. The concentrate was absorbed on silica gel and purified by flash column chromatography with ethyl acetate followed by 12% methanol/dichloromethane to provide 115 mg the desired product. Rf=0.38 (12% methanol/dichloromethane).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was absorbed on silica gel
  3. custompurified by flash column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-5abe58e1334e4a13a08db1de6bc4fb3b
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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