Triethylamine → HCID 53888912, compound

HRID 1598008Notes

Reaction equation

HRID 1598008 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)-1methylethylamine (0.163 g), and triethyamine (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-80f171825f574588b87983680f9b6566
Source dataset
uspto-grants-1998_04
Patent number
US05736554

Reaction notes

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