Tetrahydrofuran → HCID 11384187, compound

HRID 1243195Notes

Reaction equation

HRID 1243195 reaction equation
C([C:5](C1C=CC=CC=1)(C1C=CC=CC=1)[C@@:6](O[SiH3])([N:8]1[C:13]2=[N:14][C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:16][CH:17]=[C:12]2[CH2:11][N:10]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:9]1=[O:33])[CH3:7])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:66]1CCCC1>>[OH:66][CH2:5][C@H:6]([N:8]1[C:13]2=[N:14][C:15]([NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:16][CH:17]=[C:12]2[CH2:11][N:10]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:9]1=[O:33])[CH3:7]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 137329820HCID 137329820, compound

Product 1

HCID 11384187HCID 11384187, compound

Procedure

(R)-1-(2-tert-Butyl-diphenyl-silanyloxy-1-methyl-ethyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.55 g, 0.80 mmol) was dissolved in anhydrous tetrahydrofuran (6 mL) and treated with tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 3.2 mL, 3.20 mmol) (Aldrich) at 40° C. for 3 hours and then at room temperature for 2 hours. The reaction was concentrated. The residue was redissolved in ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated. Purification by flash chromatography (Biotage 40M, ethyl acetate-hexanes gradient [75–85% ethyl acetate]) followed by crystallization from ethyl acetate-hexanes gave (R)-(−)-1-(2-hydroxy-1-methyl-ethyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 0.26 g, 79.9%). Melting Point: 156–163° C.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was redissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Biotage 40M, ethyl acetate-hexanes gradient [75–85% ethyl acetate])
  7. customfollowed by crystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-4c1a897a2de94a3e92e779c3825908bd
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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