Trifluoroacetic acid → 4-(Pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 510224Notes

Reaction equation

HRID 510224 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C:9]=2[N:10]=[CH:11][N:12]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]2[CH2:16][CH2:15][NH:14][CH2:13][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733265tert-Butyl 4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Product 1

HCID 580260644-(Pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product of Example 11, step a (157 mg, 0.50 mmol) in DCM (3 mL) was added TFA (1.00 mL). After stirring 3 h the mixture was concentrated in vacuo and loaded directly on a Prep Agilent system with a XBridge C18 OBD 50×100 mm column eluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min to afford the desired product as a tan solid (89 mg, 83%). MS (ESI) mass calcd. C12H12N4, 212.11. m/z found 213.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.05 (s, 1H), 8.71 (s, 1H), 8.06-7.94 (m, 1H), 7.93-7.81 (m, 1H), 7.45-7.32 (m, 1H), 4.17 (s, 2H), 3.16 (s, 4H).

Workup

  1. concentrationwas concentrated in vacuo
  2. washeluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min

Sources & evidence

ORD record
ord-f4579781849e41f58ce0c85ba9dd4d77
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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