Hexamethylphosphoramide → HCID 13544732, compound

HRID 1020714Notes

Reaction equation

HRID 1020714 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[CH3:17][NH:18][CH2:19][CH2:20][C:21]#[N:22].CN(C)P(N(C)C)(N(C)C)=O>C(O)(C)C>[ClH:16].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:18]([CH2:19][CH2:20][C:21]#[N:22])[CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 69656Propanenitrile, 3-(methylamino)-HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamine

Product 1

HCID 13544732HCID 13544732, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

50 gms, 0.208 moles of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 21.2 gms, 0.252 moles of 3-methylaminopropionitrile were charged in a round bottom flask containing 350 ml hexamethylphosphoramide. The reaction mass was stirred at about 100° C. for 9 hours, cooled to a temperature of 25° C. and then charged with 250 ml isopropanol. The reaction mass was further stirred for 15 minutes, filtered and washed with 50 ml isopropanol and subjected to drying at 50° C. for 7-8 hours to yield N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine hydrochloride (43 gms).

Workup

  1. temperaturecooled to a temperature of 25° C.
  2. stirringThe reaction mass was further stirred for 15 minutes
  3. filtrationfiltered
  4. washwashed with 50 ml isopropanol
  5. customto drying at 50° C. for 7-8 hours

Sources & evidence

ORD record
ord-8878d411d06542fda798ef97a1ed81f0
Source dataset
uspto-grants-2014_05
Patent number
US08716476B2

Reaction notes

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