5-Bromo-2-chloropyrimidin-4-ol → 2-[(5-bromo-2-chloro-6-oxo-1(6H)-pyrimidinyl)methyl]-3-Thiophenecarbonitrile

HRID 2105316Notes

Reaction equation

HRID 2105316 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][C:5]([Cl:8])=[N:6][CH:7]=1.Br[CH2:11][C:12]1[S:13][CH:14]=[CH:15][C:16]=1[C:17]#[N:18]>>[Br:1][C:2]1[C:3](=[O:9])[N:4]([CH2:11][C:12]2[S:13][CH:14]=[CH:15][C:16]=2[C:17]#[N:18])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 111601145-Bromo-2-chloropyrimidin-4-olHCID 225036202-(Bromomethyl)thiophene-3-carbonitrile

Product 1

HCID 114389322-[(5-bromo-2-chloro-6-oxo-1(6H)-pyrimidinyl)methyl]-3-ThiophenecarbonitrileYield 58%

Procedure

The title compound was prepared in 58% yield from 2-chloro-5-bromo-3H-pyrimidin-4-one (Example 1A) and 2-bromomethyl-thiophene-3-carbonitrile according to the general procedure outlined for Example 1B. 1H NMR (400 MHz, CDCl3): δ 8.10 (s, 1H), 7.40 (d, 1H, J=5.6 Hz), 7.21 (d, 1H, J=5.6 Hz), 5.74 (s, 2H). MS (ES) [m+H] calc'd for C10H5N3OSBrCl, 330, 332; found 330, 332.

Sources & evidence

ORD record
ord-ac76415a5cea459fab2507d31cbd3445
Source dataset
uspto-grants-2009_08
Patent number
US07579357B2

Reaction notes

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