Tetrahydrofuran → HCID 69584260, compound

HRID 1243180Notes

Reaction equation

HRID 1243180 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]3[N:15]([C@:28](O[SiH3])([CH3:46])[C:29](C4C=CC=CC=4)(C4C=CC=CC=4)C(C)(C)C)[C:16](=[O:27])[N:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:18][C:12]3=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[F-:49].C([N+](CCCC)(CCCC)CCCC)CCC.[O:67]1CCCC1>>[OH:67][CH2:29][C@@H:28]([N:15]1[C:13]2=[N:14][C:9]([NH:8][C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=3)=[N:10][CH:11]=[C:12]2[CH2:18][N:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][C:24]=2[F:49])[C:16]1=[O:27])[CH3:46]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131725975HCID 131725975, compound

Product 1

HCID 69584260HCID 69584260, compound

Procedure

(S)-7-(4-Fluoro-phenylamino)-1-(2-tert-butyl-diphenyl-silanyloxy-1-methyl-ethyl)-3-(4-methoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.30 g, 0.45 mmol) was dissolved in anhydrous tetrahydrofuran (3.5 mL) and treated with tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.80 mL, 1.80 mmol) (Aldrich) at room temperature for 6 hours. The reaction was then 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 40S, ethyl acetate-hexanes gradient [60–100% ethyl acetate]) followed by crystallization from ethyl acetate-hexanes gave (S)-(+)-1-(2-hydroxy-1-methyl-ethyl)-3-(2-fluoro-4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.13 g, 66.2%). Melting Point: 188–198° C.

Workup

  1. concentrationThe reaction was then 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 40S, ethyl acetate-hexanes gradient [60–100% ethyl acetate])
  7. customfollowed by crystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-7f1065a6f504425eb15f4c66f9d1e4ea
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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