Bromine → HCID 18470190, compound

HRID 2228924Notes

Reaction equation

HRID 2228924 reaction equation
CN1C=CC(=O)NC1=S.[Br:10]Br.[CH3:12][N:13]1[CH:18]=[CH:17][C:16](=[O:19])[N:15]=[C:14]1[S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:29]>ClCCl>[CH3:12][N:13]1[CH:18]=[CH:17][C:16](=[O:19])[N:15]=[C:14]1[S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)=[O:29].[CH3:12][N:13]1[CH:18]=[C:17]([Br:10])[C:16](=[O:19])[N:15]=[C:14]1[S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)=[O:29]

Participants

6

Reactant 3

HCID 24408BromineHCID 30363051H,3H-Pyrimidine-4-one-2-thione, 1-methyl-HCID 18470190HCID 18470190, compound

Product 2

HCID 18470190HCID 18470190, compoundHCID 18470340HCID 18470340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thiopyrimidin-4-one was prepared from 1-methyl-2-thiouracil by general method A4. A solution of bromine (0.05 ml) in dichloromethane (1 ml) was added to a slurry of 1-methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thiopyrimidin-4-one (0.38 g) in dichloromethane (20 ml), and the mixture was stirred for 24 hours. The solution was washed with aqueous sodium carbonate, dried and evaporated. Chromatography (silica, 1-4% methanol in dichloromethane) gave 1-methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-bromopyrimidin-4-one (0.18 g), as a white solid. 1H-NMR (CDCl3) δ 1.3-1.5 (6H, m), 1.65-1.8 (4H, m), 2.94 (2H, t), 3.26(2H, t), 3.56(3H, s), 7.45(2H, d), 7.56(1H, s) and 7.90(2H, d); MS (APCI+) found (M+1)=459; C19H22BrClN2O2S requires 458.

Workup

  1. washThe solution was washed with aqueous sodium carbonate
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-4d4c3f8520124fc29f8d11d70ccf3c54
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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