Butylamine → 7-Deaza-2'-C-methyladenosine

HRID 1391977Notes

Reaction equation

HRID 1391977 reaction equation
C1(=O)[N:5]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([C@@H:15]4[O:30][C@H:29]([CH2:31][O:32]C(C5C=CC(C)=CC=5)=O)[C@@H:18]([O:19]C(C5C=CC(C)=CC=5)=O)[C@@:16]4([CH3:42])[OH:17])[C:8]=3[N:9]=[CH:10][N:11]=2)C(=O)C2=CC=CC=C12.C(N)CCC>CO>[NH2:5][C:6]1[C:7]2[CH:14]=[CH:13][N:12]([C@@H:15]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:18]([OH:19])[C@@:16]3([CH3:42])[OH:17])[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 112391664-Phthalimido-7-[3,5-di-o-(p-toluoyl)-2-c-methyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 30118937-Deaza-2'-C-methyladenosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the toluene solution from Step B at ambient temperature were added methanol (25 L) and n-butylamine (3.13 kg, 42.9 mol). The reaction mixture was aged at 64° C. for 24 to 30 h. The mixture was concentrated to about 9 L, and 9 L of methanol was added. The solution was concentrated to 9 L, and the resulting slurry was aged at 60° C. for 60 min. Toluene (13 L) was added over 1.5 h. The slurry was aged at 60° C. for another 2 h and then allowed to cool to ambient temperature. The solid was filtered and the wet cake was washed with 9 L of 20% methanol in toluene then 9 L of 10% methanol in toluene. The solid was suction dried at ambient temperature under nitrogen to give 1.79 kg (94 wt % pure) of the title nucleoside 4-3 as the toluene solvate.

Workup

  1. concentrationThe mixture was concentrated to about 9 L, and 9 L of methanol
  2. additionwas added
  3. concentrationThe solution was concentrated to 9 L
  4. waitthe resulting slurry was aged at 60° C. for 60 min
  5. additionToluene (13 L) was added over 1.5 h
  6. waitThe slurry was aged at 60° C. for another 2 h
  7. filtrationThe solid was filtered
  8. washthe wet cake was washed with 9 L of 20% methanol in toluene
  9. customdried at ambient temperature under nitrogen

Sources & evidence

ORD record
ord-0981e2f1fed94f3080029236217d0e9e
Source dataset
uspto-grants-2008_03
Patent number
US07339054B2

Reaction notes

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