Potassium Carbonate → 2-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

HRID 30966Notes

Reaction equation

HRID 30966 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH:13]3[C:17]([OH:19])([CH3:18])[CH:16]([OH:20])[CH:15]([CH2:21][OH:22])[O:14]3)[C:4]=2[N:5]=[CH:6][N:7]=1.S([CH2:33][N+:34]#[C-:35])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[O:12][CH:35]=[N:34][CH:33]=3)=[CH:9][N:8]([CH:13]3[C:17]([CH3:18])([OH:19])[CH:16]([OH:20])[CH:15]([CH2:21][OH:22])[O:14]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 210408384-Chloro-7-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde

Product 1

HCID 866235892-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

Procedure

To the compound from Step 1 is added tosylmethyl isocyanide (1 eq.) in MeoH containing K2CO3 (1 eq.) and the mixture is heated to reflux until starting material is consumed. The solvent is removed in vacuo and the crude mixture purified by RP HPLC on a Phenominex column (250×20 mm) using a gradient of acetonitrile in water from 0 to 30% over 30 minutes at 10 mL/minute.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux
  3. customis consumed
  4. customThe solvent is removed in vacuo
  5. customthe crude mixture purified by RP HPLC on a Phenominex column (250×20 mm)
  6. customover 30 minutes

Sources & evidence

ORD record
ord-6d206b288f4f4fe3bfd4e00b07aee231
Source dataset
uspto-grants-2008_09
Patent number
US07425547B2

Reaction notes

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