Water → HCID 51348661, compound

HRID 401048Notes

Reaction equation

HRID 401048 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:24]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:27][C:26](=[O:42])[NH:25]2)[CH:17]=[C:18]([O:21][CH2:22][CH3:23])[C:19]=1[OH:20].O>C1COCC1>[CH2:22]([O:21][C:18]1[C:19]2[O:20][C:6](=[O:7])[NH:13][C:14]=2[CH:15]=[C:16]([CH:24]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:27][C:26](=[O:42])[NH:25]2)[CH:17]=1)[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 67061109HCID 67061109, compound

Product 1

HCID 51348661HCID 51348661, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of CDI (243 mg, 1.50 mmol) in THF (3 mL) was added 4-(3-amino-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (386 mg, 0.96 mmol) and the resultant mixture was heated to reflux for 1.0 h. The reaction mixture was added water (10 mL) and filtered. The filtered mass was washed with methanol (3 mL) and dried to afford Compound 72 as a yellow solid (110 mg, 30%). 1H NMR (DMSO-d6 500 MHz): δ 11.56 (s, 1H), 8.69 (s, 1H), 7.49 (s, 1H), 7.21 (s, 3H), 7.20 (s, 2H), 6.99-7.04 (m, 3H), 6.81 (d, J=6.0 Hz, 2H), 6.74 (d, J=6.0 Hz, 2H), 5.12 (s, 1H), 4.11 (q, J=6.8 Hz, 2H), 1.31 (t, J=7.0 Hz, 3H); MS (ESI): m/z 428.1 [M+1]+.

Workup

  1. temperatureto reflux for 1.0 h
  2. filtrationfiltered
  3. washThe filtered mass was washed with methanol (3 mL)
  4. customdried

Sources & evidence

ORD record
ord-a33cb8eed09c47fe8c36ee7e6fdd6158
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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