Methanol → HCID 53836724, compound

HRID 1461695Notes

Reaction equation

HRID 1461695 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][C:11](=O)[N:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9]2)=[CH:4][N:3]=1.S(C)C.CO>O1CCCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9]2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 19892025HCID 19892025, compound

Product 1

HCID 53836724HCID 53836724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-aminopyrimid-5-yl)-4-(1,1-dimethylethyl)-5-oxo-morpholine (2.0 g) in 100 ml of dry tetrahydrofuran, 10 ml of a 2.0M solution of BH3.Me2S in tetrahydrofuran is added dropwise under nitrogen. The reaction mixture is then heated at reflux for 5 hours followed by treatment with methanol (25 ml) at reflux for 3 hours. The solution is concentrated and the residue chromatographed on silica gel to give the titled compound.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux for 5 hours
  3. temperatureat reflux for 3 hours
  4. concentrationThe solution is concentrated
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-e5e79599a649402a843cef93991bcec5
Source dataset
uspto-grants-1991_12
Patent number
US05077290

Reaction notes

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