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Water → (2-Amino-6-{2-[(cyclopropylmethylamino)methyl]phenyl}quinazolin-4-yl)-(1,3-dihydroisoindol-2-yl)methanone

HRID 1631155
Notes
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Reaction equation

HRID 1631155 reaction equation
Br[C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]1[CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:21][C:22]1[N:31]=[C:30]([C:32]([N:34]2[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35]2)=[O:33])[C:29]2[C:24](=[CH:25][CH:26]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[N:23]=1>C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:21][C:22]1[N:31]=[C:30]([C:32]([N:34]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:42]2)=[O:33])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:2]3[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=3[CH2:4][NH:5][CH2:6][CH:7]3[CH2:9][CH2:8]3)[CH:28]=2)[N:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 28431311[(2-Bromophenyl)methyl](cyclopropylmethyl)amineHCID 58457219[2-Amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

Product 1

HCID 89675009(2-Amino-6-{2-[(cyclopropylmethylamino)methyl]phenyl}quinazolin-4-yl)-(1,3-dihydroisoindol-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

114 mg of (2-bromobenzyl)cyclopropylmethylamine, 100 mg of potassium carbonate, 7 μl of water and 29 mg of [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride are added to a solution of 150 mg of [2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 5 ml of ethanol under argon. The mixture is heated at 120° C. for 30 min; the hot mixture is filtered through kieselguhr, the filtrate is evaporated and purified by chromatography (reversed phase HPLC).

Workup

  1. filtrationthe hot mixture is filtered through kieselguhr
  2. customthe filtrate is evaporated
  3. custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record
ord-4e72c1b18f87406e82145774d652f6c3
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes