Dibutyltin oxide → HCID 178525388、化合物

HRID 870588ノート

反応式

HRID 870588 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])=[O:22])[CH2:18][CH2:17][C:15]=2[N:16]=1.[N:29]([Si](C)(C)C)=[N+:30]=[N-:31].C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1.ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[O:22])[CH2:18][CH2:17][C:15]=2[N:16]=1

参加物

6

反応物 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 867265503-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

生成物 1

HCID 178525388HCID 178525388、化合物収率 41%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

Heat a solution of 3-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.24 g; 1.0 equiv; 0.64 mmoles), azidotrimethylsilane (0.85 mL; 10 equiv; 6.38 mmoles) and dibutyloxostannane (0.040 g; 0.25 equiv; 0.16 mmoles) in toluene (5 mL) to 100° C. for 24 hours, then cool to ambient temperature and concentrate. Purify the crude material by reverse phase chromatography to afford impure product. Dissolve the impure product in 50 mL dichloromethane and wash with saturated sodium bicarbonate, and further extract the aqueous layer 2× dichloromethane. Dry the combined organic extracts over sodium sulfate, filter, and concentrate to afford 3-(1H-tetrazol-5-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.110 g; 41%) as a yellow solid: MS (m/z): 421 (M+1).

後処理

  1. concentrationconcentrate
  2. customPurify the crude material by reverse phase chromatography
  3. customto afford impure product
  4. washwash with saturated sodium bicarbonate
  5. extractionfurther extract the aqueous layer 2× dichloromethane
  6. dry with materialDry the combined organic extracts over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

出典と根拠

ORDレコード
ord-939d1667a7594c01ae680122bd6e27b1
出典データセット
uspto-grants-2015_03
特許番号
US08969555B2

反応ノート

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