Sodium Methoxide → 9-Deaza-9-(3-thienylmethyl)guanine

HRID 266227노트

반응식

HRID 266227 반응식
C([N:5]([C:13]1[C:17]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)=[CH:16][NH:15][C:14]=1[C:24]([O:26]C)=O)[C:6]([NH:8]C(OC)=O)=[NH:7])(OC)=O.C[O-].[Na+]>CO>[NH2:7][C:6]1[NH:8][C:24](=[O:26])[C:14]2[NH:15][CH:16]=[C:17]([CH2:18][C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[C:13]=2[N:5]=1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 140382079HCID 140382079, 화합물

생성물 1

HCID 1355124689-Deaza-9-(3-thienylmethyl)guanine수율 85%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 3-(N,N'-bis-carbomethoxyguanidinyl)-4-(3-thienylmethyl)-1H-pyrrole-2-carboxylate, obtained from Example 23 (3.94 g, 0.01 mol), sodium methoxide (1.62 g, 0.03 mol) and methanol (100 mL) were stirred together and boiled under reflux for six hours. The solvent was evaporated in vacuo and the residue was treated with water (200 mL) containing acetic acid (10 mL). The solid was collected by filtration and crystallized from ethanol to give 2.1 g (85%) of 2-amino-7-(3-thienylmethyl)-4-oxo-3H,5H-pyrrolo[3,2-d]pyrimidine as pale-yellow needles, mp 222°-224° C. with gas evolution, followed by resolidification and remelting at 268°-270° C. (lit.1 271°-272° C.).

후처리

  1. temperatureunder reflux for six hours
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was treated with water (200 mL)
  4. additioncontaining acetic acid (10 mL)
  5. filtrationThe solid was collected by filtration
  6. customcrystallized from ethanol

출처 및 근거

ORD 기록
ord-21b3279b8c984897b6eef77edcb53c98
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650511

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