Trifluoroacetic acid → 5-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51524

反応式

HRID 51524 の反応式
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:9]=2)=[CH:16][CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 22736379tert-butyl4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-piperidinecarboxylate

生成物 1

HCID 101615435-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine収率 92.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-piperidinecarboxylate (0.69 g, 1.4 mmol) in dry CH2Cl2 (25 ml) at 0° C. was added TFA (5 ml). The solution was stirred at room temperature for 20 hr and the solvent evaporated. NaOH solution (5N, 10 ml) was added and the resulting slurry was extracted with EtOAc (3×50 ml). Wash with brine (1×50 ml). Dry, filter and concentrate to leave a solid which was triturated with diethylether and filtered to leave 5-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (433258) as a white solid (500 mg, 91%). M.pt 209-211° C. Rf in 1:1 EtOAc : MeOH=0.1. 1H NMR (d6 DMSO, 250 MHz) 8.13 (1H, s), 7.36-7.48 (4H, m), 7.29 (1H, s), 7.04-7.16 (5H, m), 5.80 (2H, bs), 4.64 (1H, m), 3.10 (2H, m), 2.80 (1H, bs), 2.67 (2H, m), 1.94 (4H, m). Mass spec. C23H23ON5 (385.1902). IR (KBr disc): 3278, 1620, 1585, 1490, 1245 cm−1.

後処理

  1. customthe solvent evaporated
  2. additionNaOH solution (5N, 10 ml) was added
  3. extractionthe resulting slurry was extracted with EtOAc (3×50 ml)
  4. washWash with brine (1×50 ml)
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto leave a solid which
  9. customwas triturated with diethylether
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-05cff2dd24b34503aed78dae107a8f09
出典データセット
uspto-grants-2004_03
特許番号
US06713474B2

関連ノート

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