Triethylamine → 3-(5-Amino-6-chloro-2-propylthiopyrimidine-4-ylamino)-5-(hydroxymethyl)-cyclopentane-1,2-diol

HRID 2255899Notes

Reaction equation

HRID 2255899 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([S:10][CH2:11][CH2:12][CH3:13])[N:3]=1.[NH2:14][CH:15]1[CH2:19][CH:18]([CH2:20][OH:21])[CH:17]([OH:22])[CH:16]1[OH:23].C(N(CC)CC)C>C(O)CCC>[NH2:8][C:7]1[C:2]([NH:14][CH:15]2[CH2:19][CH:18]([CH2:20][OH:21])[CH:17]([OH:22])[CH:16]2[OH:23])=[N:3][C:4]([S:10][CH2:11][CH2:12][CH3:13])=[N:5][C:6]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2767383-Amino-5-(hydroxymethyl)cyclopentane-1,2-diolHCID 114363364,6-Dichloro-2-(propylthio)pyrimidin-5-amine

Product 1

HCID 190286923-(5-Amino-6-chloro-2-propylthiopyrimidine-4-ylamino)-5-(hydroxymethyl)-cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The product of step iv) (4.6 g) was added to a solution of 3-amino-5-(hydroxymethyl)-cyclopentane-1,2-diol (1.41 g) in butan-1-ol (200 ml) containing triethylamine (10 ml) and the whole heated to reflux for 48 hours. Evaporation gave a dark residue which was chromatographed (SiO2, 10% ethanol/dichloromethane) to afford the sub-title compound (2.8 g).

Workup

  1. temperaturethe whole heated
  2. temperatureto reflux for 48 hours
  3. customEvaporation
  4. customgave a dark residue which
  5. customwas chromatographed (SiO2, 10% ethanol/dichloromethane)

Sources & evidence

ORD record
ord-4871f2a537e94655b876e156cfd75ce7
Source dataset
uspto-grants-1997_08
Patent number
US05654285

Reaction notes

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