Methylhydrazine → HCID 15747245, compound

HRID 1450679Notes

Reaction equation

HRID 1450679 reaction equation
C1(=O)[N:5]([O:6][CH2:7][C@H:8]2[O:12][C@@H:11]([N:13]3[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]3=[O:15])[CH2:10][C@@H:9]2[O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)C(=O)C2=CC=CC=C12.CNN>C(Cl)Cl>[NH2:5][O:6][CH2:7][C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 15747244HCID 15747244, compound

Product 1

HCID 15747245HCID 15747245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 5'-O-phthalimido-3'-O-tert-butyl(diphenyl)silylthymidine in dry CH2Cl2 (10 ml) was added methylhydrazine (3 mmol) under anhydrous conditions at room temperature. The solution was stirred for 12 hrs, cooled (0° C.) and filtered. The precipitate was washed with CH2Cl2 (2×10 ml) and combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, 20 g). Elution with CH2Cl2 :MeOH (9:1, v/v) furnished the desired 5'-O-amino-3'-O-tert-butyl(diphenyl)silylthymidine as a crystalline product (65%): 1H NMR (CDCl3) δ1.0 (s, 9, C(CH3)3), 1.80 (s, 3, CH3), 1.81 and 2.24 (2 m, 2, C2, CH2), 3.25 and 3.60 (2 m, 2, C5, CH2), 4.0 (m, 1, C3, H), 4.25 (m, 1, C4, H), 5.4 (v br, s, NH2), 6.25 (t, 1, C1, H), 7.2 (s, 1, C6H), 7.25-7.60 (m, 10, ArH), 8.4 (br s, 1, NH).

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with CH2Cl2 (2×10 ml)
  3. concentrationwere concentrated
  4. customThe residue was purified by flash column chromatography (silica gel, 20 g)
  5. washElution with CH2Cl2 :MeOH (9:1

Sources & evidence

ORD record
ord-91870d7cdec24803b37ad762b96ed853
Source dataset
uspto-grants-1997_02
Patent number
US05602240

Reaction notes

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