1-Propanol → HCID 67176736, compound

HRID 1027497Notes

Reaction equation

HRID 1027497 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:32]=[CH:31][C:17]([CH2:18][C:19]2[N:20]=[C:21]([OH:30])[C:22]3[N:27]=[C:26]([S:28][CH3:29])[O:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1.[CH2:33](O)[CH2:34][CH3:35].C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[CH:32]=[CH:31][C:17]([CH2:18][C:19]2[N:20]=[C:21]([O:30][CH2:33][CH2:34][CH3:35])[C:22]3[N:27]=[C:26]([S:28][CH3:29])[O:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178503362HCID 178503362, compound

Product 1

HCID 67176736HCID 67176736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 8.7 mmol of polystyrene-bound triphenylphosphine (Argonaut) and 1.5 g of diethyl azodicarboxylate (DEAD) in 55 ml of tetrahydrofuran was stirred for 15 min at 0° C. Then 2.2 g of 5-(4-chloro-benzyl)-2-methylsulfanyl-oxazolo[5,4-d]pyrimidin-7-ol, 0.65 ml of propan-1-ol and 1 ml of triethylamine were added. The reaction mixture was stirred at room temperature for 3 h. The polymer was filtered off and washed thoroughly with tetrahydrofuran. The solvent was removed in vacuo and the title compound isolated by silica gel chromatography (method SC1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. filtrationThe polymer was filtered off
  3. washwashed thoroughly with tetrahydrofuran
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-99a0da59772547ae975dc971ad8b199f
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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