tert-Butanol → HCID 21995254, compound

HRID 1977689Notes

Reaction equation

HRID 1977689 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 tert-butyl alcohol (10 ml), was added triethylamine (1,2 m, 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-c4c530951f5d418da36b91fecd3add9b
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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