Hydrochloric Acid → HCID 24962293, compound

HRID 2059571Notes

Reaction equation

HRID 2059571 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([O:19]C(=O)C4C=CC(C)=CC=4)[C@@H:13]([CH2:29][O:30]C(=O)C4C=CC(C)=CC=4)[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C[O-].[Na+].Cl>CO.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([OH:19])[C@@H:13]([CH2:29][OH:30])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86642245HCID 86642245, compound

Product 1

HCID 24962293HCID 24962293, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Crude intermediate (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(4-methylbenzoyloxy)-5-(4-methylbenzoyloxymethyl)-3-ethynyl-tetrahydro-furan-3-ol (434 mg, 0.74 mmol) is dissolved in MeOH (5 ml) and CH2Cl2 (5 ml). 30% sodium methoxide in methanol solution (1.38 ml, 7.4 mmol, 10 equiv.) is added and the mixture is stirred at room temperature for 15 mins. The mixture is neutralized to pH 7.0 by addition of 1N HCl solution and evaporated under vacuum to dry, purified by flash chromatography (CH2Cl2:MeOH=92:8) to yield (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol. 1H-NMR (CDCl3): δ 8.58 (s, 1H), 8.00 (d, 1H, J=3.9 Hz), 6.68 (d, 1H, J=3.9 Hz), 6.49 (s, 1H), 4.51 (d, 1H, J=9.0 Hz), 4.20-3.75 (m, 3H), 2.51 (s, 1H). ESI-MS: calcd. for C13H12ClN3O4 (309.05). found: 310.3.

Workup

  1. customevaporated under vacuum
  2. customto dry
  3. custompurified by flash chromatography (CH2Cl2:MeOH=92:8)

Sources & evidence

ORD record
ord-78c7db89530c4fa8b1c288697d0381c6
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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