Water → HCID 178429453, compound

HRID 576923Notes

Reaction equation

HRID 576923 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 1784917022-[(2-chloro-4-methoxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 178429453HCID 178429453, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. mixture of 2-{[(2-chloro-4-methoxyphenyl)methyl]sulfanyl}-6-methyl-pyrimidin-4-ol (500 mg, 1.7 mmol) in anhydrous dichloromethane (20 mL) was added a solution of boron tribromide (1 M in THF, 2 mL, 2 mmol). The solution was stirred at room temperature overnight. Water (20 mL) and more dichloromethane (50 mL) were added to the mixture. The undissolved solid material was recovered by filtration, washed with diethyl ether (2×25 mL), and dried in vacuo. The crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2), affording the title compound (65 mg, 13% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.37 (s, 2H), 6.00 (s (br), 1H), 6.70 (dd, 1H, J=2.3 Hz, 8.4 Hz), 6.84 (d, 1H, J=2.3 Hz), 7.40 (d, 1H, J=8.6 Hz), 9.96 (s, 1H); M+ 283; HPLC purity: 98.0%.

Workup

  1. filtrationThe undissolved solid material was recovered by filtration
  2. washwashed with diethyl ether (2×25 mL)
  3. customdried in vacuo
  4. customThe crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c270dc6ff02e459c8529a7c0799880e0
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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