2,2-Dimethylpropyl carbonochloridate → HCID 54293747, Verbindung

HRID 251493

Reaktionsgleichung

Reaktionsgleichung von HRID 251493
[CH2:1]([O:6][C:7](Cl)=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24]([NH2:26])=[N:23][CH:22]=[N:21][C:20]=3[N:19]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:18]=2)=[CH:13][C:12]=1[O:32][CH3:33]>N1C=CC=CC=1.ClCCl>[NH2:26][C:24]1[C:25]2[C:17]([C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:7](=[O:8])[O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])=[C:12]([O:32][CH3:33])[CH:13]=3)=[CH:18][N:19]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[C:20]=2[N:21]=[CH:22][N:23]=1

Komponenten

5

Edukt 2

HCID 33521852,2-Dimethylpropyl carbonochloridateHCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 54293747HCID 54293747, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Neopentylchloroformate (28 uL, 0.186 mmol) was added dropwise to a stirring solution of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.155 mmol) in pyridine (1 mL) and dichloromethane (1 mL) under nitrogen at 0° C. After 10 minutes, the ice water bath was removed and the resulting mixture was stirred for 4 hours. The solvent was evaporated and the residue was taken into ethyl acetate. The organic layer was washed, dried and evaporated. The solid was purified by preparative TLC using dichloromethane/methanol (95:5) as the mobile phase to give neopentyl N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate. 1H NMR (CDCl3) δ 1.00 (s 9H), 1.78 (m, 2H), 1.90 (m, 4H), 2.26 (m, 2H), 3.91 (s, 2H), 3.94 (s, 3H), 5.22 (m, 3H), 6.22 (s, 1H), 7.01 (s, 1H), 7.08 (d, J=8 Hz, 1H), 7.25 (s, 1H), 8.17 (br. d, 1H), 8.32 (s, 1H); LC/MS (MH+=438).

Aufarbeitung

  1. customthe ice water bath was removed
  2. customThe solvent was evaporated
  3. washThe organic layer was washed
  4. customdried
  5. customevaporated
  6. customThe solid was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-ead8163023a741d58c0a116a5a8288bd
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863444B2

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