Triethylamine → HCID 67062983, compound

HRID 599274Notes

Reaction equation

HRID 599274 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([NH:19][CH2:20][C:21]2[C:22]([NH:29][CH3:30])=[N:23][C:24]([S:27][CH3:28])=[N:25][CH:26]=2)=[C:12]([CH3:31])[CH:11]=1.CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[F:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N:19]2[CH2:20][C:21]3[C:22](=[N:23][C:24]([S:27][CH3:28])=[N:25][CH:26]=3)[N:29]([CH3:30])[C:4]2=[O:3])=[C:12]([CH3:31])[CH:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10426DiphosgeneHCID 67063060HCID 67063060, compound

Product 1

HCID 67062983HCID 67062983, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of diphosgene (0.85 mL, 7.2 mmol) in anhydrous dioxane (20 mL) was added a solution of 5-((4-fluoro-2-methyl-5-nitrophenylamino)methyl)-N-methyl-2-(methylthio)pyrimidin-4-amine (2.2 g, 6.5 mmol) and Et3N (1.32 g, 13 mmol) in anhydrous dioxane (50 ml) at 0° C. After the addition, the resulting mixture was stirred at 50° C. overnight. Water was added and the mixture was neutralized with saturated Na2CO3 solution to pH 8. The dioxane was removed in vacuo, and the aqueous layer was extracted with EtOAc (3×60 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was washed with ether and dried in vacuo to afford 3-(4-fluoro-2-methyl-5-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (2 g, 84%). 1H NMR (400 MHz, CDCl3): δ 8.04 (s, 1 H), 7.97 (d, J=8 Hz, 1 H), 7.18 (d, J=12 Hz, 1 H), 4.73 (d, J=14.8 Hz, 1 H), 4.42 (d, J=14.8 Hz, 1 H), 3.40 (s, 3 H), 2.52 (s, 3 H), 2.25 (s, 3 H); MS (ESI) m/z: 364.1 [M+H]+.

Workup

  1. additionAfter the addition
  2. customThe dioxane was removed in vacuo
  3. extractionthe aqueous layer was extracted with EtOAc (3×60 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. washThe residue was washed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c124dc959e0344bab1938fb9bbe190ca
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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