Triethylamine → HCID 53888912, compound

HRID 863778Notes

Reaction equation

HRID 863778 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-β-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 hexane/ethyl 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 hexane/ethyl acetate

Sources & evidence

ORD record
ord-4fb4216753d949e7b6b65e46efb03976
Source dataset
uspto-grants-1996_10
Patent number
US05561134

Reaction notes

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