Triethylamine → (1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol

HRID 1507477Notes

Reaction equation

HRID 1507477 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([O:9][CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.Cl.[NH2:14][C@@H:15]1[CH2:19][C@H:18]([CH2:20][OH:21])[C@@H:17]([OH:22])[C@H:16]1[OH:23].C(N(CC)CC)C>CCO>[OH:21][CH2:20][C@H:18]1[CH2:19][C@@H:15]([NH:14][C:2]2[C:7]([I:8])=[C:6]([O:9][CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=2)[C@H:16]([OH:23])[C@@H:17]1[OH:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734536(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol Hydrochloride2×HCID 117677754HCID 117677754, compound

Product 1

HCID 117677905(1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

Compound 3 (5.00 g, 15.7 mmol) and (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (Compound 4) (5.80 g, 31.6 mmol) were dissolved in EtOH (50 mL). Triethylamine (6.60 mL, 47.4 mmol) was added, the reaction was sealed, and heated to 130° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (EtOAc/hexanes) to give the title compound as a colorless oil. LCMS 1.23 min, 428 (M+H).

Workup

  1. customthe reaction was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified via column chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-6649a51ee5704c4b8bb8c8294eb35f19
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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