2,6-Di-tert-butyl-4-methylpyridine → HCID 86607324, compound

HRID 552739Notes

Reaction equation

HRID 552739 reaction equation
[CH2:1]([C:3]1[C:11]2[CH:10]=[N:9][CH:8]=[N:7][C:6]=2[N:5]([C@@H:12]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[CH2:13]2)[CH:4]=1)[CH3:2].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[C:35]([O:39][C:40](=[O:46])[NH:41][S:42](Cl)(=[O:44])=[O:43])([CH3:38])([CH3:37])[CH3:36]>C(C#N)(C)=O>[C:35]([O:39][C:40](=[O:46])[NH:41][S:42]([O:18][CH2:17][C@@H:15]1[C@@H:14]([OH:19])[CH2:13][C@H:12]([N:5]2[C:6]3[N:7]=[CH:8][N:9]=[CH:10][C:11]=3[C:3]([CH2:1][CH3:2])=[CH:4]2)[O:16]1)(=[O:44])=[O:43])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 67164234HCID 67164234, compound

Product 1

HCID 86607324HCID 86607324, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

To a solution of (2R,3S,5R)-5-(5-ethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol (0.0560 g, 0.213 mmol) and 2,6-di-tert-butyl-4-methylpyridine in AcCN (4 mL) at 0° C. was added tert-butyl(chlorosulfonyl)carbamate (0.0573 g, 0.266 mmol), the solution was warmed to room temperature and stirred for 1 hour. The reaction was quenched with 7N ammonia in methanol (2 mL) and concentrated. The residue was purified by flash chromatography (0 to 10% MeOH/DCM) to give the title compound as a white solid (39 mg, 29%).

Workup

  1. customThe reaction was quenched with 7N ammonia in methanol (2 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-be624c2ddfdf448a8b1e00a3abc836c5
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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