Phosphorus sulfide (P2S5) → HCID 178476363, compound

HRID 19481Notes

Reaction equation

HRID 19481 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:32]>N1C=CC=CC=1>[NH2:1][C:2]1[NH:3][C:4](=[S:32])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 1354347855-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione

Product 1

HCID 178476363HCID 178476363, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 25 (1 g, 2.26 mmol) in pyridine (50 mL) was added at room temperature P2S5 (2.13 g, 4.79 mmol). The solution was refluxed gently (bath temperature 130-140° C.) for 29 h. The reaction mixture was evaporated to dryness in vacuo. The excess P2S5 was decomposed by the addition of H2O (40 mL) at 60° C. The mixture was stirred for 1 h at 60° C. and then cooled to room temperature. The mixture was extracted with CHCl3 (3×40 mL). The dried (MgSO4) organic layer was evaporated to yield a syrup, which was purified by flash column chromatography (silica, acetone/CHCl3=15%) to afford 0.93 g (90%) of 77 as a yellow solid: 1H (400 MHz, d6-DMSO) δ 12.50 (s, 1H), 7.35 (br s, 2H), 5.89 (m, 2H), 5.51 (t, J=6.4 Hz, 1H), 4.36 (dd, J=12.0, 4.0 Hz, 1H), 4.24 (m, 1H), 4.10 (q, J=6.0 Hz, 1H), 2.07 (s, 3H), 2.06 (s, 3H), 2.01 (s, 3H); MS (+)-ES [M+H]+ m/z 459.3.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. additionThe excess P2S5 was decomposed by the addition of H2O (40 mL) at 60° C
  3. temperaturecooled to room temperature
  4. extractionThe mixture was extracted with CHCl3 (3×40 mL)
  5. dry with materialThe dried (MgSO4) organic layer
  6. customwas evaporated
  7. customto yield a syrup, which
  8. customwas purified by flash column chromatography (silica, acetone/CHCl3=15%)

Sources & evidence

ORD record
ord-d56ed34721ba447f8d2b2b948b547a21
Source dataset
uspto-grants-2010_06
Patent number
US07745415B2

Reaction notes

Loading…