Triphenylphosphine → HCID 86760470, compound

HRID 459982Notes

Reaction equation

HRID 459982 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([S:23][CH3:24])=[N:19][CH:20]=2)[NH:15][C:14]1=[O:25].[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34](O)[CH2:33][CH2:32]1)=[O:30])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([N:15]2[C:16]3=[N:17][C:18]([S:23][CH3:24])=[N:19][CH:20]=[C:21]3[CH2:22][N:13]([C:3]3[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[F:12])[C:14]2=[O:25])[CH2:33][CH2:32]1)=[O:30])[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 18445159HCID 18445159, compound

Product 1

HCID 86760470HCID 86760470, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 250-mL dry, round-bottomed flask was added 3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-methylsulfanyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidine (1.5 g, 4.08 mmol), ethyl-4-hydroxycyclohexanecarboxylate (2.11 g, 12.23 mmol), triphenylphosphine (3.21 g, 12.23 mmol), and tetrahydrofuran (50 mL), and the solution was blanketed with a nitrogen atmosphere. The solution was then cooled to 0° C., and diisopropylazodicarboxylate (2.41 mL, 12.23 mmol) was added dropwise. The solution was then warmed to room temperature and stirred overnight. The crude mixture was then concentrated in vacuo and taken up in dichloromethane, washed with water, dried over sodium sulfate, and concentrated. The crude was purified by flash silica chromatography eluting with 3:2 hexane/ethyl acetate to yield the title compound (1.17 g, 55% yield): LRMS: 523.2 (M+H).

Workup

  1. customTo a 250-mL dry
  2. temperatureThe solution was then warmed to room temperature
  3. concentrationThe crude mixture was then concentrated in vacuo
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude was purified by flash silica chromatography
  8. washeluting with 3:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-9e54ba409d1a4d71ac46dcacd7d47e46
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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