Purine → HCID 18670198, compound

HRID 1059441Notes

Reaction equation

HRID 1059441 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.[N:20]1[CH:28]=[C:27]2[C:23]([N:24]=[CH:25][NH:26]2)=[N:22][CH:21]=1.[H-].[Na+]>CN(C)C=O>[N:20]1[CH:28]=[C:27]2[C:23]([N:24]([CH2:2][C:3]3[CH:4]=[CH:5][C:6]4[S:11][C:10]5[N:12]=[CH:13][CH:14]=[N:15][C:9]=5[N:8]([CH2:16][O:17][CH3:18])[C:7]=4[CH:19]=3)[CH:25]=[N:26]2)=[N:22][CH:21]=1.[N:20]1[CH:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:2][C:3]2[CH:4]=[CH:5][C:6]3[S:11][C:10]4[N:12]=[CH:13][CH:14]=[N:15][C:9]=4[N:8]([CH2:16][O:17][CH3:18])[C:7]=3[CH:19]=2)=[N:22][CH:21]=1

Participants

6

Reactant 3

HCID 1044PurineHCID 24758Sodium hydrideHCID 1133536310-methoxymethyl-8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 2

HCID 18670198HCID 18670198, compoundHCID 18670348HCID 18670348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with the procedure of Example 1094, 740 mg of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine was reacted with 460 mg of purine in the presence of sodium hydride (60% oily) in N,N-dimethylformamide (10 ml). The two isomers thus obtained were purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 320 mg of 8-(purin-9-ylmethyl)-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 125 mg of 8-(purin-7-ylmethyl)-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine each as yellow crystals.

Workup

  1. customThe two isomers thus obtained
  2. customwere purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-edacafd417fc4e4ba835c3d4c851d713
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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