2,6-Di-tert-butyl-4-methylpyridine → tert-Butyl {[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate

HRID 222160Notes

Reaction equation

HRID 222160 reaction equation
[C@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:24][C@H:23]([OH:25])[C@H:22]([CH2:26][OH:27])[CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.Cl[S:44]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])(=[O:46])=[O:45]>C(C#N)(C)=O>[C:50]([O:49][C:48](=[O:54])[NH:47][S:44]([O:27][CH2:26][C@@H:22]1[CH2:21][C@@H:20]([N:17]2[C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][C@H:1]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:3][CH2:2]4)[C:12]=3[CH:19]=[CH:18]2)[CH2:24][C@@H:23]1[OH:25])(=[O:46])=[O:45])([CH3:53])([CH3:51])[CH3:52]

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 66618256(1S,2S,4R)-4-{-4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol

Product 1

HCID 86614247tert-Butyl {[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamateYield 37%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

(1S,2S,4R)-4-{4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol (27.6 mg, 0.117 mmol) and 2,6-di-tert-butyl-4-methylpyridine (48.5 mg, 0.236 mmol) were suspended in AcCN (1.57 mL) and cooled to 0° C. tert-Butyl (chlorosulfonyl)carbamate was added and the mixture was allowed to warm to rt overnight. The reaction was quenched via addition of MeOH (1.00 mL) and concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (15.2 mg, 37%). LC/MS: Rt=1.29 min, ES+ 544 (FA standard).

Workup

  1. additionwas added
  2. customThe reaction was quenched via addition of MeOH (1.00 mL)
  3. concentrationconcentrated in vacuo
  4. washSilica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-7c7a89e2fe3245ad9219ba3e7889c57a
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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