Triethylamine → 5-((Benzyloxy)methyl)-2-butyl-7-(5-(4-isopropylpiperazin-1-yl)pent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1487255ノート

反応式

HRID 1487255 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)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][CH:33]([N:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][C:44]#[CH:45])[CH2:37][CH2:36]1)[CH3:34]>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>[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:45]#[C:44][CH2:43][CH2:42][CH2:41][N:38]2[CH2:39][CH2:40][N:35]([CH:33]([CH3:34])[CH3:32])[CH2:36][CH2:37]2)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 901769325-((Benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amineHCID 901770341-iso-Propyl-4-(pent-4-yn-1-yl)piperazine2 回

生成物 1

HCID 1184538115-((Benzyloxy)methyl)-2-butyl-7-(5-(4-isopropylpiperazin-1-yl)pent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine収率 31.1%

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3 回HCID 22036561Dimethyl sulfoxide methanol溶媒

実験手順

To a degassed solution of 5-((benzyloxy)methyl)-2-butyl-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine (223 mg, 0.511 mmol) in anhydrous N,N-dimethylformamide (3.5 mL) under a nitrogen atmosphere at room temperature was added copper(I) iodide (19 mg, 0.10 mmol), bis(triphenylphosphine)palladium(II)dichloride (40 mg, 0.057 mmol) and finally triethylamine (0.128 mL, 0.920 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 (159 mg, 0.818 mmol) in anhydrous degassed N,N-dimethylformamide (0.5 mL) was added. The reaction mixture was stirred at 55° C. for 40 minutes. A solution of 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine 60 mg (0.309 mmol) in anhydrous degassed N,N-dimethylformamide (0.5 mL) was added. The reaction mixture was stirred at 55° C. for 30 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 oil was dissolved in MeOH:DMSO (1:1) (4×1 mL) and purified by MDAP (Method B) Appropriate fractions were combined and evaporated in vacuo to yield the title compound as a yellow oil (80 mg).

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 55° C. for 40 minutes
  3. additionwas added
  4. stirringThe reaction mixture was stirred at 55° C. for 30 minutes
  5. customThe reaction was evaporated in vacuo
  6. customto yield a dark yellow oil
  7. customThe oil was partitioned between water and dichloromethane
  8. customThe organic layer was separated
  9. extractionthe aqueous back extracted with dichloromethane
  10. customevaporated in-vacuo
  11. customto yield a dark yellow oil
  12. custompurified by MDAP (Method B) Appropriate fractions
  13. customevaporated in vacuo

出典と根拠

ORDレコード
ord-4be3db3f5e244f128211f7edc0429ecc
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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