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Water → HCID 25215195, compound

HRID 2194770
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Reaction equation

HRID 2194770 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([CH3:39])[CH:38]=1)[C:6]([C:8]1[N:13]([CH2:14][C:15]2([CH2:18][C:19]([NH:21]CC3C=CC(OC)=CC=3)=[O:20])[CH2:17][CH2:16]2)[C:12](=[O:31])[NH:11][C:10](=[O:32])[C:9]=1[CH:33]([CH3:35])[CH3:34])=[O:7])#[N:2].O>C(#N)C.C(O)(=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([CH3:39])[CH:38]=1)[C:6]([C:8]1[N:13]([CH2:14][C:15]2([CH2:18][C:19]([NH2:21])=[O:20])[CH2:16][CH2:17]2)[C:12](=[O:31])[NH:11][C:10](=[O:32])[C:9]=1[CH:33]([CH3:35])[CH3:34])=[O:7])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 962WaterHCID 582034682-{1-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-cyclopropyl}-N-(4-methoxy-benzyl)-acetamide

Product 1

HCID 25215195HCID 25215195, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342
Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-{1-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-cyclopropyl}-N-(4-methoxy-benzyl)-acetamide (97 mg, 0.18 mmol) in acetonitrile (4 mL) and glacial acetic acid (1 mL) at room temperature, were added ceric ammonium nitrate (201 mg, 0.36 mmol) and water (2 mL) in this order. After stirring for 20 min., the mixture was diluted with ethyl acetate, washed with water twice, dried with MgSO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, from ethyl acetate to 10% methanol in ethyl acetate) to give 59 mg (78%) of 2-{1-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-cyclopropyl}-acetamide (85) as a white solid. m.p. 283-285° C.; 1H-NMR (500 MHz, DMSO-d6) δ 0.20-0.27 (2H, m), 0.31-0.36 (1H, m), 0.43-0.47 (1H, m), 0.99 (3H, d, J=6.8 Hz), 1.08 (3H, d, J=6.8 Hz), 2.02-2.13 (2H, m), 2.17 (1H, d, J=16.5 Hz), 2.44 (3H, s), 3.32 (1H, d, J=15.1 Hz), 3.39-3.41 (1H, m), 3.46-3.51 (1H, m), 3.79 (1H, d, J=15.1 Hz), 8.08 (1H, s), 8.19 (1H, s), 8.42 (1H, s), 11.45 (1H, s); m/z (EI) 408 (M+).

Workup

  1. washwashed with water twice
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, from ethyl acetate to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-990a7daf1a5c45d08482953b79a9e795
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes