2,2-Dimethyl-1,3-propanediamine → 9-bromo-3,3-dimethyl-3,4-dihydro-1H-pyrimido[2,1-b]quinazolin-6(2H)-one

HRID 1619348Notes

Reaction equation

HRID 1619348 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1/[N:11]=[C:12]1\C(Cl)=NSS\1.[CH3:19][C:20]([CH3:25])([CH2:23][NH2:24])[CH2:21][NH2:22]>C1COCC1>[Br:10][C:7]1[CH:6]=[C:5]2[C:4]([C:3](=[O:18])[N:22]3[CH2:21][C:20]([CH3:25])([CH3:19])[CH2:23][NH:24][C:12]3=[N:11]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 817702,2-Dimethyl-1,3-propanediamineHCID 178497427HCID 178497427, compound

Product 1

HCID 1363599489-bromo-3,3-dimethyl-3,4-dihydro-1H-pyrimido[2,1-b]quinazolin-6(2H)-oneYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-methyl-4-bromo-2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)benzoate (0.1 g, 0.27 mmol) and 2,2-dimethylpropane-1,3-diamine (28 mg, 0.27 mmol) in dry THF was stirred for 2 h at room temperature, then the solvent was evaporated to give the crude product, which was purified by column chromatography to give 80 mg of the title compound. MS (ESI): 308, 310 (MH+).

Workup

  1. customthe solvent was evaporated
  2. customto give the crude product, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-071434e0084b402288bdf0acd0861f65
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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