Trifluoroacetic acid → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one

HRID 632833Notes

Reaction equation

HRID 632833 reaction equation
COC1C=CC(C[O:8][C:9]2[C:14]([N:15]3[CH2:25][CH2:24][C:18]4[N:19]=[C:20]([NH2:23])[N:21]=[CH:22][C:17]=4[CH2:16]3)=[C:13]([CH3:26])[CH:12]=[CH:11][N:10]=2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH2:23][C:20]1[N:21]=[CH:22][C:17]2[CH2:16][N:15]([C:14]3[C:9](=[O:8])[NH:10][CH:11]=[CH:12][C:13]=3[CH3:26])[CH2:25][CH2:24][C:18]=2[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1212495386-{2-[(4-Methoxybenzyl)oxy]-4-methylpyridin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 1212495913-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-{2-[(4-methoxybenzyl)oxy]-4-methylpyridin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (3.92 g, 10.39 mmol) in dichloromethane (150 ml) was treated with trifluoroacetic acid (5.71 ml, 76.89 mmol) at room temperature. After stirring for 30 minutes, the solvent and excess acid was removed in vacuo and the residue was treated with ethyl acetate. Washing with sat'd NaHCO3(aq.) gave a yellow, amorphous precipitate. The solid was collected, washed with water, EtOAc, and dried in vacuo at 50° C. to give (1.65 g, 62%). HPLC analysis showed the compound has a purity of 97%.

Workup

  1. customthe solvent and excess acid was removed in vacuo
  2. additionthe residue was treated with ethyl acetate
  3. washWashing with sat'd NaHCO3(aq.)
  4. customgave a yellow, amorphous precipitate
  5. customThe solid was collected
  6. washwashed with water, EtOAc
  7. customdried in vacuo at 50° C.
  8. customto give (1.65 g, 62%)

Sources & evidence

ORD record
ord-da951314195844d5878e1c0540df9757
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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