Hydrochloric Acid → 6-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 924822Notes

Reaction equation

HRID 924822 reaction equation
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:26][C:25](=[O:27])[NH:24][CH:23]([C:28]4[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[C:31]([OH:37])=[C:30]([O:38][CH2:39][CH3:40])[CH:29]=4)[C:22]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:26][C:25](=[O:27])[NH:24][CH:23]([C:28]3[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[C:31]([OH:37])=[C:30]([O:38][CH2:39][CH3:40])[CH:29]=3)[C:22]=2[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866693306-(4-(diphenylmethyleneamino)phenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

Product 1

HCID 513483616-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-oneYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-(diphenylmethyleneamino)phenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one (230 mg, 0.38 mmol) in THF (2 mL) was added concentrated HCl solution (0.5 mL), and the mixture was stirred at room temperature for 2 h. The mixture was concentrated and purified by column to give Compound 57 (170 mg, yield 100%). 1H NMR (DMSO-d6 400 MHz): δ 10.31 (s, 1H), 8.54 (s, 1H), 7.50 (s, 1H), 7.45 (s, 1H), 7.22 (d, J=1.6 Hz, 1H), 7.07-6.97 (m, 5H), 6.83 (d, J=7.2 Hz, 2H), 6.59 (d, J=7.2 Hz, 2H), 5.09 (d, J=2.8 Hz, 1H), 4.06 (q, J=6.8 Hz, 2H), 1.34 (t, J=6.8 Hz, 3H); MS (ESI): m/z 447.0 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column

Sources & evidence

ORD record
ord-072ea0efaa4741f0b340744dfd6a38be
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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