Ethyl Bromide → HCID 135995106, compound

HRID 1970928Notes

Reaction equation

HRID 1970928 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[N:5][C:4]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:3]1[C:20]#[N:21].[CH2:22](N(CC)CC)[CH3:23].BrCC>CN(C=O)C.ClCCl>[CH2:22]([N:17]1[CH2:16][CH2:15][N:14]([C:4]2[N:5]=[C:6]([CH2:8][C:9]3[CH:13]=[CH:12][S:11][CH:10]=3)[NH:7][C:2](=[O:1])[C:3]=2[C:20]#[N:21])[CH2:19][CH2:18]1)[CH3:23]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 8471TriethylamineHCID 135995116HCID 135995116, compound

Product 1

HCID 135995106HCID 135995106, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

50 mg (0.17 mmol) of 6-oxo-4-(piperazin-1-yl)-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile are dissolved together with 34 mg (0.33 mmol) of triethylamine in DMF and, after addition of 19.9 mg (0.18 mmol) of bromoethane, stirred at RT overnight. The mixture is then diluted with dichloromethane and washed with water. The organic phase is separated off and dried over sodium sulphate, and the residue is flash-chromatographed on silica gel (mobile phase: dichloromethane/methanol 100:1, 80:1, 60:1, 40:1). 38 mg (70% of theory) of the title compound are obtained.

Workup

  1. washwashed with water
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. customthe residue is flash-chromatographed on silica gel (mobile phase: dichloromethane/methanol 100:1, 80:1, 60:1, 40:1)

Sources & evidence

ORD record
ord-72c49b5d8bd946d2ae96963a2d4014b4
Source dataset
uspto-grants-2013_04
Patent number
US08431573B2

Reaction notes

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