Triethylamine → HCID 53888912, compound

HRID 381687Notes

Reaction equation

HRID 381687 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:12]1[O:13][CH3:14].[Cl:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH2:27][C@H:28]([NH2:30])[CH3:29].C(N(CC)CC)C>C(O)C>[Cl:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH2:27][C@H:28]([NH:30][C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:11]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:12]1[O:13][CH3:14])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15682117HCID 15682117, compoundHCID 18656685HCID 18656685, compound

Product 1

HCID 53888912HCID 53888912, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-9-(2′-O-methyl-b-D-ribofuranosyl)-9H-purine (prepared as in EP Publication No. 0378518) (0.28 g), 2-(3-chloro-2-thienyl)-(1R)-1-methylethylamine (0.163 g), and triethylamine (0.5 mL) in ethanol (30 mL) is refluxed for about 18 hours, cooled and concentrated in vacuo. The residue is purified by flash chromatography, eluting with 10% methanol in methylene chloride, followed by crystallization from hexanelethyl acetate, to give the desired product, m.p. 75-76° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by flash chromatography
  4. washeluting with 10% methanol in methylene chloride
  5. customfollowed by crystallization from hexanelethyl acetate

Sources & evidence

ORD record
ord-957a7898df284c7a92c956191e3001fa
Source dataset
uspto-grants-2001_10
Patent number
US06307054B1

Reaction notes

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