Ethyl chloroformate → 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl ethyl carbonate

HRID 1984101Notes

Reaction equation

HRID 1984101 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:27])[C:5]2[C:10]([C:11]#[C:12][CH2:13][CH2:14][OH:15])=[CH:9][N:8]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:6]=2[N:7]=1.[H-].[Na+].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(N(C)C)=O>[C:31](=[O:32])([O:33][CH2:34][CH3:35])[O:15][CH2:14][CH2:13][C:12]#[C:11][C:10]1[C:5]2[C:4]([Cl:27])=[N:3][C:2]([NH2:1])=[N:7][C:6]=2[N:8]([CH2:16][C:17]2[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 119505104-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol

Product 1

HCID 577138224-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl ethyl carbonate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (1.53 g) and NaH (95%, 0.38 g) in anhydrous DMA (25 mL) was treated with ethyl chloroformate (1.5 mL) at 0-23° C. for 0.5 h. Work-up and preparative HPLC gave the title compound. HPLC Rt=5.65 min.

Sources & evidence

ORD record
ord-d8274a1452e44ff8b63f88f735197af1
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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