Triethylamine → 9-(2-Phthalimidoethoxymethyl)guanine hydrate

HRID 614951ノート

反応式

HRID 614951 の反応式
C[Si]([C:5]1[NH:13][C:12]2[C:11](=[O:14])[NH:10][C:9]([N:15]([Si](C)(C)C)[Si](C)(C)C)=[N:8][C:7]=2[N:6]=1)(C)C.Cl[CH2:25][O:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(O)C>[OH2:14].[C:30]1(=[O:39])[N:29]([CH2:28][CH2:27][O:26][CH2:25][N:6]2[CH:5]=[N:13][C:12]3[C:11](=[O:14])[NH:10][C:9]([NH2:15])=[N:8][C:7]2=3)[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]12

参加物

6

反応物 3

HCID 8471TriethylamineHCID 12926790N-(2-chloromethoxyethyl)phthalimideHCID 136139236Tris-(trimethylsilyl)guanine

生成物 1

HCID 1363987959-(2-Phthalimidoethoxymethyl)guanine hydrate収率 172.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

To a stirred solution of tris trimethylsilylguanine (16.5 g) in toluene (50 ml) was added N-(2-chloromethoxyethyl)phthalimide (17.0 g) and triethylamine (23 ml). The reaction mixture was heated at reflux under nitrogen for 29 hours, cooled and evaporated under reduced pressure giving a dark brown oil. The oil was digested in ethanol (400 ml) on a steam bath for 40 minutes, giving a solid which was collected and washed with ethanol and ether. It was recrystallized from 2-methoxyethanol to give 9-(2-phthalimidoethoxymethyl)guanine hydrate (14.4 g), m.p. >240° C. (dec.). A mixture of 9-(2-phthalimidoethoxymethyl)guanine hydrate (0.94 g), hydrazine (2 ml) and ethanol (100 ml) was heated at reflux with stirring for one hour. The reaction mixture was filtered hot, and the filtrate was cooled and evaporated under reduced pressure. Ethanol was added and the mixture re-evaporated. This was repeated three times. The residual solid was stirred with 3% aqueous acetic acid (50 ml) for 30 minutes and filtered. The solids were washed with water (15 ml), and the wash and filtrate combined. The combined wash and filtrate was evaporated under reduced pressure at <35° C. to a small volume, diluted with ethanol and evaporated to dryness. The pasty, white solid was dispersed in a small amount of ethanol and diluted with a few ml ether to give a granular solid which was collected, washed with ethanol and dried. Recrystallization from ethanol-water gave 9-(2-aminoethoxymethyl)guanine acetate monohydrate (0.43 g), m.p. (~135° C. melts and resolidifies) 174°-176° C.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 29 hours
  3. temperaturecooled
  4. customevaporated under reduced pressure
  5. customgiving a dark brown oil
  6. customgiving a solid which
  7. customwas collected
  8. washwashed with ethanol and ether
  9. customIt was recrystallized from 2-methoxyethanol

出典と根拠

ORDレコード
ord-1b2728a3bed849d489632e64705485f9
出典データセット
uspto-grants-1979_03
特許番号
US04146715

反応ノート

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