tert-Butanol → HCID 21995254, compound

HRID 619373Notes

Reaction equation

HRID 619373 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.C([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[N:29]=1)(O)=O.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[C:47]([O:51][C:23]([NH:20][C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]2[CH:36]=[C:37]([O:45][CH3:46])[C:38]([O:43][CH3:44])=[C:39]([O:41][CH3:42])[CH:40]=2)[N:29]=1)=[O:8])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 21995247HCID 21995247, compound

Product 1

HCID 21995254HCID 21995254, compound

Procedure

To a solution of diphenylphosphorylazide (0.92 ml, 4.3 mmol) in tertbutyl alcohol (10 ml), was added triethylamine (1,2 ml, 8.5 mmol) and 4-carboxy-N-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine (1.0 g, 2.9 mmol), [see Example 121] and the mixture heated at reflux for 2 h. After this time the solvent was evaporated and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated under reduced pressure. Column chromatography [silica 2% methanol CH2Cl2 ] gave the title compound (850 mg) as a light yellow solid m.p. 124°. δH (CDCl3) 8.27 (1H, d, J 5.8 Hz), 7.45 (1H, br s), 7.32 (1H, d, J 5.8 Hz), 7.20 (1H, br s), 6.81 (2H, s), 3.85 (6H, s), 3.81 (3H, s) and 1.53 (9H, s). MS m/z 377 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 h
  3. customAfter this time the solvent was evaporated
  4. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  5. washThe organic layer was washed with water (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-867f99ccffb84ae187baff069c9783f2
Source dataset
uspto-grants-1999_09
Patent number
US05958935

Reaction notes

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