HCID 178497680、化合物 → HCID 178497681、化合物

HRID 1108265ノート

反応式

HRID 1108265 の反応式
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:24]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CO.[Pd]>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:29]([CH3:30])[CH3:31])([CH:26]([CH3:27])[CH3:28])[CH:32]([CH3:34])[CH3:33])[CH:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

参加物

4

反応物 1

HCID 178497680HCID 178497680、化合物

生成物 1

HCID 178497681HCID 178497681、化合物収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of methyl 4-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethynyl]-1-triisopropylsilylpyrrole-2-carboxylate (550 mg, 1.0 mmol) and 10% palladium-on-carbon (220 mg) in methanol (45 mL) was stirred overnight under hydrogen (50 psi). The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo. The residue was dissolved in methylene chloride and filtered through a short silica gel column. The eluate was evaporated to give methyl 4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-1-triisopropylsilylpyrrole-2-carboxylate (524 mg, 94%). The analytical sample, mp 202-204° C., was obtained by column chromatography using chloroform:methanol (19:1): 1H NMR (CDCl3) δ 11.34 (br s, 1H), 7.85 (br s, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 4.69 (s, 1H), 3.79 (s, 3H), 3.36 (br d, 1H, J=10.0 Hz), 2.99 (m, 1H), 2.83 (m, 1H), 2.59 (m, 2H), 2.12 (dd, 1H, J=15.6, 9.0 Hz), 1.90-1.50 (m, 6H), 1.30 (s, 9H), 1.11 (d, 18H, J=7.6 Hz).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered through a short silica gel column
  5. customThe eluate was evaporated

出典と根拠

ORDレコード
ord-79bab5c82e024e24864ebc4917b36854
出典データセット
uspto-grants-2000_05
特許番号
US06066639

反応ノート

読み込み中…