Triethylamine → HCID 118453797、化合物

HRID 1487256ノート

反応式

HRID 1487256 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 118453797HCID 118453797、化合物収率 33.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒2 回HCID 22036561Dimethyl sulfoxide methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b79ca8b1040342af9b6c78894c3586ae
出典データセット
uspto-grants-2016_08
特許番号
US09428512B2

反応ノート

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