Tetrahydrofuran → HCID 11339970, compound

HRID 1243192Notes

Reaction equation

HRID 1243192 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH2:19][C:18]2[C:13](=[N:14][C:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[N:16][CH:17]=2)[N:12]([C@:29](O[SiH3])([CH3:47])[C:30](C2C=CC=CC=2)(C2C=CC=CC=2)C(C)(C)C)[C:11]1=[O:50].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:69]1CCCC1>>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH2:19][C:18]2[C:13](=[N:14][C:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[N:16][CH:17]=2)[N:12]([C@@H:29]([CH3:47])[CH2:30][OH:69])[C:11]1=[O:50]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131725977HCID 131725977, compound

Product 1

HCID 11339970HCID 11339970, compound

Procedure

(S)-3-(2-Fluoro-4-methoxy-phenyl)-1-(2-tert-butyl-diphenyl-silanyloxy-1-methyl-ethyl)-7-(4-methoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.25 g, 0.35 mmol) was dissolved in anhydrous tetrahydrofuran (2.5 mL) and treated with tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.40 mL, 1.400 mmol). The reaction was stirred in a water bath that was maintained in the 30–40° C. range. The reaction was complete after 4 hours and was concentrated. This residue was redissolved in ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, concentrated and then purified by flash chromatography (Biotage 40S, 75:25 ethyl acetate-hexanes) to give (S)-(+)-3-(2-fluoro-4-methoxy-phenyl)-1-(2-hydroxy-1-methyl-ethyl)-7-(4-methoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a pale yellow foam. (Yield 0.14 g, 85.1%).

Workup

  1. temperaturewas maintained in the 30–40° C. range
  2. concentrationwas concentrated
  3. dissolutionThis residue was redissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by flash chromatography (Biotage 40S, 75:25 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-5012c5b4653242c197b0de38ecdd4e1c
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

Loading…