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

HRID 266227Notes

Reaction equation

HRID 266227 reaction equation
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

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 140382079HCID 140382079, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-21b3279b8c984897b6eef77edcb53c98
Source dataset
uspto-grants-1997_07
Patent number
US05650511

Reaction notes

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