Triethylamine → HCID 67063149, compound

HRID 599260Notes

Reaction equation

HRID 599260 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]2[C:19]([NH:26][CH3:27])=[N:20][C:21]([S:24][CH3:25])=[N:22][CH:23]=2)=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29].CCN(CC)CC>O1CCOCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:17][C:18]3[C:19](=[N:20][C:21]([S:24][CH3:25])=[N:22][CH:23]=3)[N:26]([CH3:27])[C:4]2=[O:3])=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 67063020HCID 67063020, compound

Product 1

HCID 67063149HCID 67063149, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of diphosgene (3.5 g, 17.7 mmol) in dioxane (350 mL) at 0° C. was slowly added a solution comprised of 5-((4-fluoro-3-nitrophenylamino)methyl)-N-methyl-2-(methylthio)pyrimidin-4-amine (5.2 g, 16.1 mmol) and Et3N (4.5 mL, 32.1 mmol) in dioxane (250 mL). The resultant reaction mixture was stirred at RT overnight. The solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The combined organics were dried (Na2SO4) and concentrated to give crude product, which was washed with cold MeOH (5 mL) to give 3-(4-fluoro-3-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (5.0 g, 89% yield) as a brown solid. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (s, 1 H), 8.20 (m, 1 H), 7.82 (m, 1 H), 7.64 (dd, J=6.9, 8.4 Hz, 1 H), 4.82 (s, 2 H), 3.29 (s, 3 H), 2.50 (s, 3 H); MS (ESI) m/z: 350.3 (M+H+).

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between EtOAc and H2O
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give crude product, which
  7. washwas washed with cold MeOH (5 mL)

Sources & evidence

ORD record
ord-c2f02c6a5e4c488c84500c0b027e712b
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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