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

HRID 6247

반응식

HRID 6247 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 84166Methanol, 1,1-diethoxy-, 1-acetate용매

반응 조건

온도
120 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-ca0089c60afa41788d06a4e5994a6587
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

연결된 노트

불러오는 중…