Triethylamine → tert-Butyl 4-(5-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)pent-4-yn-1-yl)piperazine-1-carboxylate

HRID 1487253Notes

Reaction equation

HRID 1487253 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][CH2:27][CH2:28]Cl)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].C(N(CC)CC)C>CN(C)C=O.CO.CS(C)=O>[NH2:19][C:17]1[C:18]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[C:12]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][N:40]3[CH2:39][CH2:38][N:37]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:42][CH2:41]3)[C:13]=2[N:14]=[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])[N:16]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 143452tert-Butyl piperazine-1-carboxylate2×HCID 1184166305-((Benzyloxy)methyl)-2-butyl-7-(5-chloropent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Product 1

HCID 131736840tert-Butyl 4-(5-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)pent-4-yn-1-yl)piperazine-1-carboxylateYield 58.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-((benzyloxy)methyl)-2-butyl-7-(5-chloropent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (100 mg, 0.243 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added 1-BOC-piperazine (50 mg, 0.268 mmol) and triethylamine (51 νL, 0.366 mmol). The reaction was stirred at 70° C. for 22 hours. A further 100 mg (0.537 mmol) of 1-BOC-piperazine and 0.1 mL (0.717 mmol) of triethylamine was added to the reaction. The reaction was stirred at 70° C. for a further 24 hours. The cooled reaction was evaporated in vacuo and partitioned between dichloromethane and water. The organic layer was passed through a hydrophobic frit and evaporated in vacuo to yield a yellow 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 colourless oil (80 mg).

Workup

  1. stirringThe reaction was stirred at 70° C. for a further 24 hours
  2. customThe cooled reaction
  3. customwas evaporated in vacuo
  4. custompartitioned between dichloromethane and water
  5. customevaporated in vacuo
  6. customto yield a yellow oil
  7. custompurified by MDAP (Method B)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-36b6028b58234a8980ea15fdf86e9300
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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