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

HRID 1487259Notes

Reaction equation

HRID 1487259 reaction equation
[NH2:1][C:2]1[C:3]2[N:14]([CH2:15][O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]=[C:12]([C:24]#[C:25][CH2:26][N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)[C:4]=2[N:5]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[N:7]=1.Cl>CO.O1CCOCC1.CO.CS(C)=O>[CH2:17]([O:16][CH2:15][N:14]1[C:3]2[C:2]([NH2:1])=[N:7][C:6]([CH2:8][CH2:9][CH2:10][CH3:11])=[N:5][C:4]=2[C:12]([C:24]#[C:25][CH2:26][N:27]2[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]2)=[CH:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 118453806tert-Butyl 4-(3-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)prop-2-yn-1-yl)piperazine-1-carboxylate

Product 1

HCID 1184537845-((Benzyloxy)methyl)-2-butyl-7-(3-(piperazin-1-yl)prop-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 54.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a solution of tert-butyl 4-(3-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)prop-2-yn-1-yl)piperazine-1-carboxylate (85 mg, 0.160 mmol) in anhydrous methanol (5 mL) was added 4M hydrogen chloride in 1,4-dioxane (0.5 ml, 2.0 mmol). The reaction was stirred at room temperature for 19 hours. A further 0.5 mL (2.0 mmol) of 4M hydrogen chloride in 1,4-dioxane was added to the reaction. Reaction stirred at room temperature for 2 hours. The reaction was evaporated to dryness under a stream of nitrogen to yield a green oil. The oil was dissolved in MeOH:DMSO (1:1) (2×1 mL) and purified by MDAP (Method B). Appropriate fractions were combined and evaporated in-vacuo to yield the title compound as a pale yellow oil (38 mg).

Workup

  1. customReaction
  2. stirringstirred at room temperature for 2 hours
  3. customThe reaction was evaporated to dryness under a stream of nitrogen
  4. customto yield a green oil
  5. custompurified by MDAP (Method B)
  6. customevaporated in-vacuo

Sources & evidence

ORD record
ord-0af1cb8248da43a0b99003ea1ed50f5c
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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