Benzyl mercaptan → 7-(benzylthio)quinazolin-4(3H)-one

HRID 1473407Notes

Reaction equation

HRID 1473407 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:55]([SH:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.CCN(C(C)C)C(C)C>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:55]([S:62][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

8

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 1364090647-(benzylthio)quinazolin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A round bottom flask was charged with 7-bromoquinazolin-4(3H)-one (10 g, 44.4 mmol), Xantphos (1.286 g, 2.222 mmol), and Pd2(dba)3 (1.017 g, 1.111 mmol). The flask was flushed with Ar (g), then dioxane (89 ml), benzyl mercaptan (5.52 ml, 46.7 mmol), and n,n-diisopropylethylamine (15.52 ml, 89 mmol) were added in sequence. The reaction was fitted with a reflux condenser, heated to 90° C., and stirred for one hour. The reaction was diluted with water and filtered. The solids were washed thoroughly with water, then air dried for several hours and triturated with ethyl acetate. After stirring overnight, the solids were filtered, washed with ethyl acetate, and vacuum dried over a nitrogen blanket overnight to afford 7-(benzylthio)quinazolin-4(3H)-one as a light yellow solid. (ESI) 269.1 (M+H)+.

Workup

  1. customThe flask was flushed with Ar (g)
  2. customThe reaction was fitted with a reflux condenser
  3. filtrationfiltered
  4. washThe solids were washed thoroughly with water
  5. customair dried for several hours
  6. customtriturated with ethyl acetate
  7. stirringAfter stirring overnight
  8. filtrationthe solids were filtered
  9. washwashed with ethyl acetate, and vacuum
  10. customdried over a nitrogen blanket overnight

Sources & evidence

ORD record
ord-85789a104b724511b348466ea575a23e
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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