Carbonic acid-guanidine (1:1) → HCID 11703845, compound

HRID 2176962Notes

Reaction equation

HRID 2176962 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=2)[C:3]=1[C:4]#[N:5].C(=O)(O)O.[NH2:23][C:24]([NH2:26])=[NH:25]>CC(N(C)C)=O>[I:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:2]3[C:3]=2[C:4]([NH2:5])=[N:25][C:24]([NH2:26])=[N:23]3)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 65489737HCID 65489737, compound

Product 1

HCID 11703845HCID 11703845, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Fluoro-6-(4-iodobenzyloxy)benzonitrile (176.6 mg, 0.5 mmol) and guanidine carbonate (110 mg; 0.6 mmol) were heated at 140° C. in dimethyl acetamide for 7 hours. The mixture was cooled to room temperature and stored in the freezer overnight. The precipitate was collected by filtration and the filtrate was diluted with dichloromethane. The filtrate was stored in the freezer for 3 hours. The resulting precipitate was collected by filtration and all the solids were combined and crystallized from 50% ethanol/water to yield 114 milligrams of 5-(4-iodobenzyloxy)quinazoline-2,4-diamine.

Workup

  1. customstored in the freezer overnight
  2. filtrationThe precipitate was collected by filtration
  3. additionthe filtrate was diluted with dichloromethane
  4. filtrationThe resulting precipitate was collected by filtration and all the solids
  5. customcrystallized from 50% ethanol/water

Sources & evidence

ORD record
ord-ce54761d26374e5eb2eb511e3f9625e5
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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