tert-Butanol → HCID 21995254, compound

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

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 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)+.