Methylamine → HCID 11617294, compound

HRID 659990Notes

Reaction equation

HRID 659990 reaction equation
[Cl:1][CH2:2][C:3]1[N:12]([CH2:13][CH2:14][CH3:15])[C:11](=[O:16])[C:10]2[C:5](=[C:6]([OH:19])[C:7]([Cl:18])=[CH:8][C:9]=2[Cl:17])[N:4]=1.[CH3:20][NH2:21]>C1COCC1.C(O)C>[ClH:1].[Cl:17][C:9]1[CH:8]=[C:7]([Cl:18])[C:6]([OH:19])=[C:5]2[C:10]=1[C:11](=[O:16])[N:12]([CH2:13][CH2:14][CH3:15])[C:3]([CH2:2][NH:21][CH3:20])=[N:4]2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 45118229HCID 45118229, compound

Product 1

HCID 11617294HCID 11617294, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloromethyl-5,7-dichloro-8-hydroxy-3-n-propyl-3H-quinazolin-4-one (285 mg, 0.886 mmol) in anhydrous THF (1.3 mL) was added a solution of methylamine in ethanol (7.5 mL of a 8.0M solution, 60 mmol) dropwise under an argon atmosphere. The mixture was stirred at room temperature for 18 h, then concentrated, and to the resulting residue was added 2M HCl (5 mL). The mixture was evaporated and more 2M HCl (5 mL) was added. The residue was evaporated and the procedure repeated two more times. The mixture was triturated with dichloromethane and dried in vacuo to yield 5,7-dichloro-8-hydroxy-2-methylaminomethyl-3-n-propyl-3H-quinazolin-4-one hydrochloride (4-9A) as a yellow solid (157 mg, 50%)(Table 6).

Workup

  1. concentrationconcentrated
  2. additionto the resulting residue was added 2M HCl (5 mL)
  3. customThe mixture was evaporated
  4. additionmore 2M HCl (5 mL) was added
  5. customThe residue was evaporated
  6. customThe mixture was triturated with dichloromethane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d5bafb3727184923b0f5610daa4ad0ce
Source dataset
uspto-grants-2011_12
Patent number
US08084459B2

Reaction notes

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