Imidazole → HCID 67259647, compound

HRID 1724628Notes

Reaction equation

HRID 1724628 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18]O)[C@@H:14]([OH:15])[C@H:12]1[OH:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.CC1N=CN=C2C=1NC=N2.[I:54]I>O1C=CC=C(O)C1>[CH3:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][I:54])[C@@H:14]([OH:15])[C@H:12]1[OH:13]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 9713114675-48-0HCID 52875471H-Purine, 6-methyl-

Product 1

HCID 67259647HCID 67259647, compound

Reagents, catalysts & solvents 1

HCID 22143352HCID 22143352, compoundSolvent

Procedure

The reaction is carried out according to Example 5 starting from 6-Methyl-9-(β-D-ribofuranosyl)purine (2a in Table VII) (108 mg, 0.41 mmol), triphenylphosphine (361 mg, 1.36 mmol), and imidazole (185 mg, 2.70 mmol) in M-PYROL (2 ml). Hassan et al., Convenient Synthesis of 6-Methylpurine and Related Nucleosides, Nucleosides, Nucleotides, & Nucleic Acids, 19, 1123-1134 (2000). Iodine beads (1-3 mm) (339 mg, 1.33 mmol) are added over 10 min. The resulting red solution is stirred at room temperature for 4 h at which time TLC indicated complete reaction. No further addition of reagents is required. After aqueous workup and purification by preparative TLC as described for per Example 5, pure 2b (93 mg, 61%) crystallized from 1:1 H2O/MeCN as a white solid.

Workup

  1. additionare added over 10 min
  2. customreaction
  3. additionNo further addition of reagents
  4. customAfter aqueous workup and purification by preparative TLC
  5. customcrystallized from 1:1 H2O/MeCN as a white solid

Sources & evidence

ORD record
ord-9ea23a56a2514b62a7899dccf9cdbca8
Source dataset
uspto-grants-2009_02
Patent number
US07488598B2

Reaction notes

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