Thionyl Chloride → HCID 66867721, compound

HRID 1920657Notes

Reaction equation

HRID 1920657 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[N:6]2[CH2:11][CH2:12]O.O=S(Cl)[Cl:23]>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[N:6]2[CH2:11][CH2:12][Cl:23]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66867749HCID 66867749, compound

Product 1

HCID 66867721HCID 66867721, compoundYield 27%

Procedure

0.11 g of 2-(6-amino-8-(pyridin-3-ylamino)-purin-9-yl)ethanol were cooled to −20° C. and 2 ml of SOCl2 were added. The temperature was gradually risen to 50° C. and the mixture was stirred at this temperature for 12 hours. The excess of SOCl2 was evaporated and aqueous ammonia was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was separated and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate:MeOH 20:1) to give 30 mg (27%) of the desired product. 1H-NMR (DMSO-d6): 9.10 (s, 1H); 9.0 (s, 1H); 8.35 (d, 1H); 8.20 (d, 1H); 8.05 (s, 1H); 7.30 (m, 1H); 6.65 (s, 2H, —NH2); 4.55 (t, 2H); 4.0 (t, 2H).

Workup

  1. customwas gradually risen to 50° C.
  2. customThe excess of SOCl2 was evaporated
  3. additionaqueous ammonia was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate:MeOH 20:1)

Sources & evidence

ORD record
ord-825e9951c8d441b7b70e0716def7dae7
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

Loading…