HCID 118598941, compound → 3,4-Dihydro-7-(4-pyrimidinylamino)-2h-pyrido[1,2-a]pyrazine-1,6-dione

HRID 1050326Notes

Reaction equation

HRID 1050326 reaction equation
COC1C=CC(C[N:8]2[CH2:13][CH2:12][N:11]3[C:14](=[O:25])[C:15]([NH:18][C:19]4[CH:24]=[CH:23][N:22]=[CH:21][N:20]=4)=[CH:16][CH:17]=[C:10]3[C:9]2=[O:26])=CC=1>FC(F)(F)C(O)=O>[N:22]1[CH:23]=[CH:24][C:19]([NH:18][C:15]2[C:14](=[O:25])[N:11]3[CH2:12][CH2:13][NH:8][C:9](=[O:26])[C:10]3=[CH:17][CH:16]=2)=[N:20][CH:21]=1

Participants

3

Reactant 1

HCID 118598941HCID 118598941, compound

Product 1

HCID 1185987283,4-Dihydro-7-(4-pyrimidinylamino)-2h-pyrido[1,2-a]pyrazine-1,6-dione

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(4-methoxybenzyl)-7-(pyrimidin-4-ylamino)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione (5, 0.3 g, 0.79 mmol) in trifluoroacetic acid (5 mL) was heated at 90° C. for 48 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was neutralized with saturated solution of sodium bicarbonate and the compound was extracted in 10% methanol in ethyl acetate. The organic layer was separated, dried over sodium sulphate, concentrated under reduced pressure and the residue obtained was purified via column chromatography (silica, methanol/dichloromethane=10%) to afford 7-(pyrimidin-4-ylamino)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione (Cpd. No. 1) as a beige solid. Yield: 0.12 g, 59%; MS (ESI) m/z 258 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.45 (s, 1H), 8.79-8.64 (m, 2H), 8.48 (s, 1H), 8.38 (d, J=5.9 Hz, 1H), 7.41 (dd, J=6.0, 1.3 Hz, 1H), 7.11 (d, J=7.9 Hz, 1H), 4.23-4.16 (m, 2H), 3.55-3.48 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionthe compound was extracted in 10% methanol in ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue obtained
  7. customwas purified via column chromatography (silica, methanol/dichloromethane=10%)

Sources & evidence

ORD record
ord-01330c4b50c84d949ac4aab43151542f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…