Water → 2-Chloro-6-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)purine

HRID 1080669Notes

Reaction equation

HRID 1080669 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[ClH:12].[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.[CH2:23](N(CC)CC)C.[OH2:30].C[C:32](N(C)C)=[O:33]>>[Cl:12][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([N:14]2[CH2:15][CH2:16][C:17]3[C:22](=[CH:21][C:20]([O:33][CH3:32])=[C:19]([O:30][CH3:23])[CH:18]=3)[CH2:13]2)[N:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 27347171,2,3,4-Tetrahydroisoquinoline HydrochlorideHCID 53244122,6-Dichloropurine

Product 1

HCID 233655362-Chloro-6-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)purineYield 95%

Procedure

A mixture of 5.67 g of 2,6-dichloropurine, 6.89 g of 1,2,3,4-tetrahydroisoquinoline hydrochloride and 6 g of triethylamine in 40 ml of dimethylacetamide was stirred under a nitrogen atmosphere at room temperature for 3.5 hours. The mixture was poured into 500 ml of water and stirred for 30 minutes. The solids were filtered, washed with water, pressed dry and stirred in hot methanol for 1 hour. The suspension was filtered while hot and the solids dried, 9.85 g (95% yield), m.p. 271°-276° C. dec.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe solids were filtered
  3. washwashed with water
  4. custompressed dry
  5. stirringstirred in hot methanol for 1 hour
  6. filtrationThe suspension was filtered while hot and the solids
  7. customdried

Sources & evidence

ORD record
ord-3cd4e1fd30e64ab6b6a9a843b1a9cc45
Source dataset
uspto-grants-1996_12
Patent number
US05583137

Reaction notes

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