Water → HCID 178429453, compound

HRID 629965Notes

Reaction equation

HRID 629965 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-3c47d48e451448f787f86ca6268d2257
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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