Ammonia → HCID 67063045, compound

HRID 599262Notes

Reaction equation

HRID 599262 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14](SC)=[N:15][CH:16]=3)[N:11]([CH3:21])[C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[F:8].ClC1C=C(C=CC=1)C(OO)=O.[NH3:34].O1CCOCC1>C(Cl)Cl>[NH2:34][C:14]1[N:13]=[C:12]2[N:11]([CH3:21])[C:10](=[O:22])[N:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH2:1])[CH:3]=3)[CH2:18][C:17]2=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 70297m-Chloroperbenzoic acidHCID 67063098HCID 67063098, compound

Product 1

HCID 67063045HCID 67063045, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example A1 (400 mg, 1.3 mmol) in CH2Cl2 (5 mL) was added 3-chloroperoxybenzoic acid (mCPBA) (430 mg, 2.5 mmol) in one portion. After stirring for 2 h, the reaction mixture was quenched with aq NaHCO3 and aq NaHSO3. The organic layer was separated and was washed with brine, dried Na2SO4) and concentrated in vacuo. The crude product was dissolved in DMSO (2 mL) and was treated with a solution of ammonia in dioxane (2 M, 30 ml, 60 mmol). The mixture stirred overnight at RT. The reaction was concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 7-amino-3-(3-amino-4-fluorophenyl)-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (276 mg, 77% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 7.88 (s, 1 H), 6.96 (dd, J=8.4, 6.6 Hz, 1 H), 6.68 (dd, J=6.3, 2.1 Hz, 1 H), 6.52 (br s, 2 H), 6.44 (m, 1 H), 5.18 (s, 2 H), 4.48 (s, 2 H), 3.19 (s, 3 H); MS (ESI) m/z: 289.2. (M+H+).

Workup

  1. customthe reaction mixture was quenched with aq NaHCO3 and aq NaHSO3
  2. customThe organic layer was separated
  3. washwas washed with brine, dried Na2SO4) and
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude product was dissolved in DMSO (2 mL)
  6. stirringThe mixture stirred overnight at RT
  7. concentrationThe reaction was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9ff4897c0094433e9f34ffce2dc4a29a
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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