Methanol → HCID 19789538, compound

HRID 1655852Notes

Reaction equation

HRID 1655852 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([O:26]C(=O)C)[CH2:15][S:16][C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[NH:19][CH:20]=[N:21]3)[CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+].CO>C(Cl)Cl>[OH2:26].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH:14]([OH:26])[CH2:15][S:16][C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[NH:19][CH:20]=[N:21]3)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 19789528HCID 19789528, compound

Product 1

HCID 19789538HCID 19789538, compoundYield 184.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-[1-[1-[2-pyridyl)piperazin-4-yl]-2-acetoxy-3-propanylthio]purine (0.30 g, 0.725 mmol) from Example 8in methanol (5 mL), was added anhydrous sodium bicarbonate (0.10 g, 0.725 mmol) at room temperature. After one week the methanol was removed in vacuo to give the crude product as a white solid. Silica gel flash chromatography using 10% methanol:methylene chloride gave the pure product as a white solid (0.260 g, 96.6%). mp 159°-161° C. DCI/MS (M+1) 372. 300 MHz1H NMR (DMSO-d6 and D2O) δ: 8.6 (s, 1H), 8.4 (s, 1H), 8.1 (m, 1H), 7.5 (m, 1H) 6.8 (d, 1H, J=8.59 Hz), 6.6 (m, 1H), 4.0 (m, 1H), 3.3 and 3.7 (q of q, 2H), 2.5 (m, 10H).

Workup

  1. customAfter one week the methanol was removed in vacuo
  2. customto give the crude product as a white solid

Sources & evidence

ORD record
ord-456d7147be284f3abb86f6eec2e0245d
Source dataset
uspto-grants-1993_10
Patent number
US05252569

Reaction notes

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