Sodium borohydride → 4-(4-Amino-2-fluorophenoxy)-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide

HRID 1261195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261195
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:15])=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[C:6]3[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:15])=[CH:11][C:7]=3[N:8]=[CH:9][N:10]=2)=[C:2]([F:1])[CH:28]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 594245534-(2-Fluoro-4-nitrophenoxy)-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide

Produkt 1

HCID 594244174-(4-Amino-2-fluorophenoxy)-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24385Nickel DichlorideKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 24 (1.30 g, 2.72 mmol) in anhydrous MeOH (15 mL) at room temperature under nitrogen were added NiCl2×6H2O (605 mg, 2.54 mmol) and NaBH4 (192 mg, 5.08 mmol), respectively. The reaction mixture was stirred for 50 min, concentrated, cooled to 0° C., treated with HCl (10 mL, 1M) followed by addition of NH4OH (29%) (pH 9-10), and finally extracted with AcOEt. The organic extract was successively washed with water and brine, dried over Na2SO4, filtered, and concentrated to afford the title compound 25 (450 mg, 85% yield) as a yellow solid. NMR (400 MHz, CDCl3) δ(ppm): 9.04 (t, J=5.6 Hz, 1H), 8.73 (s, 1H), 8.23 (s, 1H), 7.07 (t, J=8.8 Hz, 1H), 6.48 (dd, J=2.4 and 13.2 Hz, 1H), 6.40 (dd, J=2.4 and 8.8 Hz, 1H), 5.47 (s, 2H), 3.62-3.52 (m, 4H), 3.44 (q, J=6.8 Hz, 2H), 2.56-2.48 (m, 2H), 2.46-2.40 (m, 4H).

Aufarbeitung

  1. concentrationconcentrated
  2. additiontreated with HCl (10 mL, 1M)
  3. additionfollowed by addition of NH4OH (29%) (pH 9-10)
  4. extractionfinally extracted with AcOEt
  5. extractionThe organic extract
  6. washwas successively washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bf33ff3d7ad144fabc4d0975c152f6cb
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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