Triethylamine → HCID 67063080, compound

HRID 599279Notes

Reaction equation

HRID 599279 reaction equation
O=C(Cl)OC(Cl)(Cl)Cl.[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]=1[NH:20][CH2:21][C:22]1[C:23]([NH:30][CH3:31])=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=1.CCN(CC)CC.[C:39]([O-:42])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]=1[N:20]1[CH2:21][C:22]2[C:23](=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=2)[N:30]([CH3:31])[C:39]1=[O:42]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10426DiphosgeneHCID 67063022HCID 67063022, compound

Product 1

HCID 67063080HCID 67063080, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of diphosgene (2.1 mL, 6.8 mmol) in anhydrous dioxane (30 mL) was added a solution of 5-((2-chloro-4-fluoro-5-nitrophenylamino)methyl)-N-methyl-2-(methylthio)pyrimidin-4-amine (2.2 g, 6.2 mmol) and Et3N (1.32 g, 13 mmol) in anhydrous dioxane (30 mL) at 0° C. After complete addition, the resulting mixture was stirred at 50° C. overnight. Water was added and the mixture was basified with saturated Na2CO3 solution. The mixture was concentrated in vacuo and the residue was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residual solid was washed with ether and dried to afford 3-(2-chloro-4-fluoro-5-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.4 g, 59%). 1H NMR (400 MHz, DMSO-d6): δ 8.53 (d, J=8 Hz, 1 H), 8.26 (s, 1 H), 8.08 (d, J=12 Hz, 1 H), 4.82 (d, J=16 Hz, 1 H), 4.57 (d, J=16 Hz, 1 H), 3.29 (s, 3 H), 2.50 (s, 3 H); MS (ESI) m/z: 384.1[M+H]+.

Workup

  1. additionAfter complete addition
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionthe residue was extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. washThe residual solid was washed with ether
  8. customdried

Sources & evidence

ORD record
ord-8193999593594b7cbdc05f457ef96c32
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…