Tetrahydro-2-(2-propynyloxy)-2H-pyran → 3-[9,10-Didehydro-6-methyl-2-[3-(tetrahydropyran-2-yloxy)-1-propynyl]-8alpha-ergolinyl]-1,1-diethylurea

HRID 569324Notes

Reaction equation

HRID 569324 reaction equation
Br[C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:7][N:6]1[CH3:26].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH2:34][C:35]#[CH:36]>>[CH3:26][N:6]1[C@H:5]2[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:17]=3[C:3]([CH2:4]2)=[C:2]([C:36]#[C:35][CH2:34][O:33][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[NH:16]4)=[CH:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])[CH2:7]1.[OH:27][C:17]([CH3:15])([CH3:11])[C:3]#[CH:2]

Participants

4

Reactant 2

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 130598603-(2-Bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 2

HCID 82582-Methyl-3-butyn-2-olHCID 703955753-[9,10-Didehydro-6-methyl-2-[3-(tetrahydropyran-2-yloxy)-1-propynyl]-8alpha-ergolinyl]-1,1-diethylureaYield 25%

Procedure

Starting with 3-(2-bromo-6-methyl-8α-ergolinyl)-1,1-diethylurea, 3-(tetrahydropyran-2-yloxy)-1-propyne yields 3-[9,10-didehydro-6-methyl-2-[3-(tetrahydropyran-2-yloxy)-1-propynyl]-8α-ergolinyl]-1,1-diethylurea (25%) and 3-hydroxy-3-methyl-1-butyne yields 3-[9,10-didehydro-2-(3-hydroxy-3-methyl-1-butynyl)-6-methyl-8α-ergolinyl]-1,1-diethylurea (31%).

Sources & evidence

ORD record
ord-219f7ed9ddd141b48bd5784227ed205e
Source dataset
uspto-grants-1988_03
Patent number
US04731367

Reaction notes

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