Adenine → 3-(6-Amino-9h-purin-9-yl)propanenitrile
反応式
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.Br[CH2:12][CH2:13][C:14]#[N:15].[H-].[Na+]>CN(C=O)C>[C:14]([CH2:13][CH2:12][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])#[N:15]参加物
5
実験手順
As shown in Scheme 4, alkylation of adenine 10 with 3-bromopropionitrile in the presence of NaH in DMF gave N9-(cyanoethyl)adenine 15 in 75% yield. Reaction of 15 with methyl iodoacetate and lithium 2,2,6,6-tetramethylpiperidine (Li TMP) in THF afforded a mixture of N7-alkylated product 16 (60% yield) and N9-isomer 17 (20% yield). Reduction of the ester group in 16 with NaBH4 in wet THF13 gave N7-(hydroxyethyl)adenine 18 in 55% yield. Conversion of 18 to phosphonate 19 (60% yield) was accomplished by use of diethyl (p-toluenesulfonyloxymethane)phosphonate and sodium tert-butoxide in DMF.14 Treatment of compound 19 with Me3SiBr15 then afforded phosphonic acid 20 in 45% yield.
出典と根拠
- ORDレコード
- ord-d6d8eea3b6954217aff54361fc512c71
- 出典データセット
- uspto-grants-2004_11
- 特許番号
- US06825348B2
反応ノート
読み込み中…