5-((Benzyloxy)methyl)-2-butyl-7-(5-(4-isopropylpiperazin-1-yl)pent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine → 2-Butyl-7-(5-(4-isopropylpiperazin-1-yl)pentyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1487264Notes

Reaction equation

HRID 1487264 reaction equation
C(OC[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][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]2)=[CH:11]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd].CO.CS(C)=O>[CH2:20]([C:15]1[N:16]=[C:17]([NH2:19])[C:18]2[NH:10][CH:11]=[C:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:34]3)[C:13]=2[N:14]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 2

HCID 1184538115-((Benzyloxy)methyl)-2-butyl-7-(5-(4-isopropylpiperazin-1-yl)pent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 760727332-Butyl-7-(5-(4-isopropylpiperazin-1-yl)pentyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 35.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

5-((Benzyloxy)methyl)-2-butyl-7-(5-(4-isopropylpiperazin-1-yl)pent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (77 mg, 0.153 mmol) in ethanol (20 mL) was passed through the H-cube (settings: 45° C., full hydrogen, 1 mL/min flow rate and 10% palladium on carbon CatCart30 as the catalyst). A new 10% palladium on carbon CatCart30 cartridge was inserted into the H-cube and the solution was again passed through the H-cube (settings: 45° C., full hydrogen, 1 mL/min flow rate). The solution was evaporated in-vacuo to yield a white solid. The solid 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 white solid (21 mg).

Workup

  1. customThe solution was evaporated in-vacuo
  2. customto yield a white solid
  3. custompurified by MDAP (Method B)
  4. customthe appropriate fraction was evaporated in-vacuo

Sources & evidence

ORD record
ord-c317e864292b4f3f965b14c16a94c0df
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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