6-[3-Benzyloxy-2-(diethoxyphosphorylmethoxy)propoxyamino]-4-chloro-2,5-diformamidopyrimidine → 9-[3-Benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloro-2-formamidopurine

HRID 6247

反応式

HRID 6247 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([O:27][CH2:28][P:29]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:30])[CH2:11][O:12][NH:13][C:14]1[N:19]=[C:18]([NH:20][CH:21]=[O:22])[N:17]=[C:16]([Cl:23])[C:15]=1[NH:24][CH:25]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(OCC)OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH:10]([O:27][CH2:28][P:29]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:30])[CH2:11][O:12][N:13]1[CH:25]=[N:24][C:15]2[C:14]1=[N:19][C:18]([NH:20][CH:21]=[O:22])=[N:17][C:16]=2[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 1

HCID 197952036-[3-Benzyloxy-2-(diethoxyphosphorylmethoxy)propoxyamino]-4-chloro-2,5-diformamidopyrimidine

生成物 1

HCID 197951909-[3-Benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloro-2-formamidopurine収率 75%

試薬・触媒・溶媒 1

HCID 84166Methanol, 1,1-diethoxy-, 1-acetate溶媒

反応条件

温度
120 °C

実験手順

A solution of 6-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxyamino]-4-chloro-2,5-diformamidopyrimidine (760 mg, 1.4 mmol) in diethoxymethyl acetate (2 ml) was stirred and heated in an oil bath at 120° C. for 2 hours. After cooling to ambient temperature, the solvent was evaporated and the residue dissolved in methanol (10 ml) and 0.880 ammonia (1 ml). After 15 minutes at ambient temperature the solution was evaporated to dryness. The residue obtained was chromatographed on silica gel (dichloromethane/methanol, 98:2 as eluant) to give the title compound as a colourless oil (550 mg, 75%). IR: νmax (film), 3400, 3220, 3110, 2980, 2900, 1710, 1610, 1580, 1510, 1475, 1440, 1385, 1330, 1240, 1160, 1140, 1095, 1050, 1020, 980, 920, 820, 780, 740, 700 cm-1. 1H NMR: δH [(CD3)2SO] 1.20, 1.21 (6H, 2×t, P-(OCH2CH3)2), 3.6-3.75 (2 H, m, CHCH2), 3.8-4.15 (7H, m, CH2CHCH2, OCH2P, P-(OCH2CH3)2), 4.52 (2H, s, OCH2Ph), 4.45-4.65 (2H, m, N-OCH2), 7.25-7.40 (5H, m, Ph), 8.81 (1H, s, H-8), 9.37 (1H, br.s, NHCHO), 11.31 (1H, br.s, D2O exchangeable NHCHO). Found: C, 48.11; H, 5 37; N, 12.50%. C21H27N5O7PCl requires: C, 47.77; H, 5.16; N, 13.27%. m/z: C21H28N5O7PCl requires 528.1415; observed 528.1363 (M +H+).

後処理

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in methanol (10 ml)
  4. customAfter 15 minutes at ambient temperature the solution was evaporated to dryness
  5. customThe residue obtained
  6. customwas chromatographed on silica gel (dichloromethane/methanol, 98:2 as eluant)

出典と根拠

ORDレコード
ord-ca0089c60afa41788d06a4e5994a6587
出典データセット
uspto-grants-1993_09
特許番号
US05247085

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