Triethylamine → HCID 118453797, compound

HRID 1487256Notes

Reaction equation

HRID 1487256 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)=[C:11]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][CH:34]([N:36]1[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][C:45]#[CH:46])[CH2:38][CH2:37]1)[CH3:35]>CN(C)C=O.CS(C)=O.CO.[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>[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:46]#[C:45][CH2:44][CH2:43][CH2:42][N:39]2[CH2:40][CH2:41][N:36]([CH:34]([CH3:35])[CH3:33])[CH2:37][CH2:38]2)=[C:11]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 901770341-iso-Propyl-4-(pent-4-yn-1-yl)piperazine3×HCID 1184166535-((Benzyloxy)methyl)-2-butyl-7-iodo-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Product 1

HCID 118453797HCID 118453797, compoundYield 33.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a degassed solution of 5-((benzyloxy)methyl)-2-butyl-7-iodo-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-amine (159 mg, 0.353 mmol) in anhydrous N,N-dimethylformamide (3 mL) under a nitrogen atmosphere at room temperature was added copper (I) iodide (19 mg, 0.100 mmol), bis(triphenylphosphine)palladium(II)dichloride (40 mg, 0.057 mmol) and finally triethylamine (0.088 mL, 0.636 mmol). The mixture was stirred at room temperature under a nitrogen atmosphere for 10 minutes and then a solution of 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) in anhydrous degassed N,N-dimethylformamide (1 mL) was added. The reaction mixture was stirred at 55° C. for 40 minutes. Additional 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) was added and the reaction mixture was left to stir at 55° C. for 4 5 minutes. 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) was added and the reaction mixture was left to stir at 55° C. for 45 minutes. The reaction was evaporated in vacuo to yield a dark yellow 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 yellow oil. The crude product was dissolved in 6 mL of 50:50 DMSO/MeOH and purified by MDAP (Method B). Fractions which contained product were concentrated to give the title compound as a yellow oil (61 mg).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 55° C. for 40 minutes
  3. waitthe reaction mixture was left
  4. stirringto stir at 55° C. for 4 5 minutes
  5. waitthe reaction mixture was left
  6. stirringto stir at 55° C. for 45 minutes
  7. customThe reaction was evaporated in vacuo
  8. customto yield a dark yellow oil
  9. customThe oil was partitioned between water and dichloromethane
  10. customThe organic layer was separated
  11. extractionthe aqueous back extracted with dichloromethane
  12. customevaporated in vacuo
  13. customto yield a dark yellow oil
  14. custompurified by MDAP (Method B)
  15. concentrationwere concentrated

Sources & evidence

ORD record
ord-b79ca8b1040342af9b6c78894c3586ae
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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