2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 66674841, compound

HRID 1524875Notes

Reaction equation

HRID 1524875 reaction equation
C[N:2]([CH3:15])/[CH:3]=[CH:4]/[C:5]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[CH3:16][O:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1CN.CN1C(=O)N(C)CCC1>CCOC(C)=O.CCCCCC>[CH3:16][O:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:15][N:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH:9][CH:10]=[C:11]([C:13]#[N:14])[CH:12]=2)[C:7]1=[NH:8]

Participants

5

Reactant 3

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 5972502,4-DimethoxybenzylamineHCID 87101212HCID 87101212, compound

Product 1

HCID 66674841HCID 66674841, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The product from Example 147 Part A (1.85 g, 9.38 mmol) and 2,4-dimethoxybenzylamine (2.6 mL, 15.03 mmol) were heated with 5 mL of DMPU at 140° C. for 3 h under N2. The reaction mixture was cooled, and EtOAc/hexane (1:2) was added. The precipitate formed was filtered and dried in vacuo to give 2.5 g of the desired product. 1H-NMR (400 MHz, DMSO-d6) δ 3.72 (s, 3H, 3.81 (s, 3H), 4.95 (s, 2H), 6.10 (d, J=7.03 Hz, 1H, 6.44 (d, J=7.91 Hz, 1H), 6.57 (s, 1H), 7.02 (d, J=8.35 Hz, 1H), 7.22 (d, J=6.15 Hz, 1H) 7.68 (d, J=7.91 Hz, 1H), 7.94 (s, 1H), 8.34 (d, J=7.91 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f2fe89253c254d7fa0975985e7b54ce6
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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