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Triethylamine → 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

HRID 1487258
Notes
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Reaction equation

HRID 1487258 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](I)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:32]([N:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1)[C:33]#[CH:34]>CN(C)C=O.CO.CS(C)=O.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[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:34]#[C:33][CH2:32][N:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]3)[C:13]=2[N:14]=[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateHCID 901769325-((Benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Product 1

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-carboxylateYield 98.2%

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst
HCID 6228DimethylformamideSolvent
HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a degassed solution of 5-((benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine (150 mg, 0.344 mmol) in anhydrous N,N-dimethylformamide (3 mL) under nitrogen atmosphere at room temperature was added copper(I) iodide (13 mg, 0.068 mmol), bis(triphenylphosphine)palladium(II)dichloride (27 mg, 0.038 mmol) and, finally, triethylamine (0.086 mL, 0.619 mmol). The mixture was stirred at room temperature under nitrogen atmosphere for 10 minutes and then tert-butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate (139 mg, 0.619 mmol) was added in one portion. The reaction mixture was heated to 55° C. in a pre-heated oil bath and stirred at 55° C. for 40 minutes. The reaction was evaporated in vacuo to yield a dark brown oil. The oil was partitioned between water and dichloromethane. The organic layer was separated and the aqueous back extracted with dichloromethane. The combined organic extracts were passed through a hydrophobic frit and evaporated in vacuo to yield a dark brown 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 brown oil (180 mg).

Workup

  1. temperatureThe reaction mixture was heated to 55° C. in a pre-heated oil bath
  2. stirringstirred at 55° C. for 40 minutes
  3. customThe reaction was evaporated in vacuo
  4. customto yield a dark brown oil
  5. customThe oil was partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous back extracted with dichloromethane
  8. customevaporated in vacuo
  9. customto yield a dark brown oil
  10. custompurified by MDAP (Method B)
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0084ef530ce4d549438b2fa77273c03
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428512B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes