Triethylamine → HCID 53888912, compound

HRID 1937049Notes

Reaction equation

HRID 1937049 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 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-b29e5e58b8064283bde818aa99cdfb6f
Source dataset
uspto-grants-2002_05
Patent number
US06392049B1

Reaction notes

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