Dimethyl Sulfide → HCID 51049988, compound

HRID 390350Notes

Reaction equation

HRID 390350 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[N:13]=[C:14]4[N:19]([C:20](=[O:24])[C:21]=3[O:22]C)[CH2:18][CH2:17][O:16][C:15]4([CH3:26])[CH3:25])[N:9]=[CH:8]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.S(C)C>ClC(Cl)C>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[N:13]=[C:14]4[N:19]([C:20](=[O:24])[C:21]=3[OH:22])[CH2:18][CH2:17][O:16][C:15]4([CH3:26])[CH3:25])[N:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 25134Boron tribromideHCID 58458918HCID 58458918, compound

Product 1

HCID 51049988HCID 51049988, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(1-(4-fluorobenzyl)-1H-imidazol-4-yl)-3-methoxy-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (0.042 g, 0.109 mmol, 1.0 equiv) in dichloroethane (1.1 mL) under a nitrogen atmosphere, was added BBr3.SMe2 (0.137 g, 0.437 mmol, 4.0 equiv). The reaction was then heated to 80° C. (oil bath). After stirring 1 h, the reaction was cooled to ambient temperature and cautiously quenched with water (5 mL). The mixture was poured into saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was purified by reverse phase preparatory HPLC to provide the title compound (0.017 g, 42% yield) as a pale gray solid. 1HNMR (400 MHz, CDCl3) δ ppm 11.34 (s, 1H), 7.59 (d, J=1.01 Hz, 1H), 7.42 (d, J=1.51 Hz, 1H), 7.20 (dd, J=8.69, 5.16 Hz, 2H), 7.05-7.13 (m, 2H), 5.16 (s, 2H), 3.95-4.08 (m, 4H), 1.58 (s, 6H); LCMS (ES+, (M+H)+) m/z 371.24.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. customcautiously quenched with water (5 mL)
  3. additionThe mixture was poured into saturated aqueous solution of NaHCO3
  4. extractionextracted with CH2Cl2 (×3)
  5. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-bd9ce8bc885a4a80aef1d77956426bf4
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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