Iodoethane → 5-((Benzyloxy)methyl)-2-butyl-7-(3-(4-ethylpiperazin-1-yl)prop-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1487260Notes

Reaction equation

HRID 1487260 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17]([NH2:19])=[N:16][C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][C:13]=2[C:12]([C:24]#[C:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33](N(CC)CC)[CH3:34].ICC>CN(C)C=O.CO.CS(C)=O>[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17]([NH2:19])=[N:16][C:15]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][C:13]=2[C:12]([C:24]#[C:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH2:32]2)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 1184537845-((Benzyloxy)methyl)-2-butyl-7-(3-(piperazin-1-yl)prop-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Product 1

HCID 1184538135-((Benzyloxy)methyl)-2-butyl-7-(3-(4-ethylpiperazin-1-yl)prop-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 69.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a solution of 5-((benzyloxy)methyl)-2-butyl-7-(3-(piperazin-1-yl)prop-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (38 mg, 0.088 mmol) in anhydrous N,N-dimethylformamide (1 mL) at room temperature was added triethylamine (25 μL, 0.179 mmol) and iodoethane (10 μL, 0.125 mmol). The reaction was stirred at room temperature for 5 hours. The reaction was evaporated in vacuo to yield a pale yellow oil. The oil was dissolved in MeOH:DMSO (1:1) (1 mL) and purified by MDAP (Method B). The appropriate fraction was evaporated in vacuo to yield the title compound as a pale yellow oil (28 mg).

Workup

  1. customThe reaction was evaporated in vacuo
  2. customto yield a pale yellow oil
  3. custompurified by MDAP (Method B)
  4. customThe appropriate fraction was evaporated in vacuo

Sources & evidence

ORD record
ord-23d2dabc017d4546a73b03b468adb457
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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