HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 4-(1-(3-(Difluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile

HRID 517237
Notes
Print preview

Reaction equation

HRID 517237 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][CH2:14][CH2:13][C:12]=3[N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([F:27])[F:26])[CH:20]=3)[C:10](=[O:28])[NH:9]2)=[CH:4][CH:3]=1.O.[CH3:30][N:31](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:27][CH:25]([F:26])[C:21]1[CH:20]=[C:19]([N:11]2[C:12]3[CH2:13][CH2:14][CH2:15][C:16](=[O:18])[C:17]=3[CH:8]([C:5]3[CH:4]=[CH:3][C:2]([C:30]#[N:31])=[CH:7][CH:6]=3)[NH:9][C:10]2=[O:28])[CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 867323224-(4-Bromophenyl)-1-(3-(difluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione2×

Product 1

HCID 867323594-(1-(3-(Difluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

Under an atmosphere of argon, a mixture of 4-(4-bromophenyl)-1-(3-(difluoromethyl)-phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione (intermediate 33, 75 mg, 0.168 mmol), zinc cyanide (34 mg, 0.290 mmol) and tetrakis(triphenylphosphine)-palladium(0) (20 mg, 17 μmol) in N,N-dimethylformamide (1 mL) is heated at 110° C. for 2 h and cooled to room temperature. Water is added and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 100:0 to 0:100). Yield: 30 mg; ESI mass spectrum [M+H]+=394; Retention time HPLC: 0.53 min (X012_S01).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture is extracted twice with dichloromethane
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 100:0 to 0:100)
  6. custom0.53 min (X012_S01)

Sources & evidence

ORD record
ord-4f85ef1125f34e6dacfe80f98c60206a
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115093B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes