Acetic Acid → (6-Ethyl-8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 2076041Notes

Reaction equation

HRID 2076041 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]2[N:18]=[CH:19][C:20]3[CH2:26][NH:25][CH2:24][CH:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]=3[N:22]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1.[CH2:33](N)[CH3:34].C(=O)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH2:33]([N:25]1[CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[N:22]=[C:17]([NH:16][C:6]3[CH:7]=[CH:8][C:9]([N:10]4[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]4)=[C:4]([O:3][CH3:2])[CH:5]=3)[N:18]=[CH:19][C:20]=2[CH2:26]1)[CH3:34]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 44194157[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochloride

Product 1

HCID 44194160(6-Ethyl-8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochloride (75 mg, 0.17 mmol) in tetrahydrofuran (3.3 mL) was added at room temperature NN,-diisoprpyl ethyl amine (43 mg, 0.33 mmol). After stirring for 5 minutes at room temperature acetaldehyde (8.1 mg, 0.18 mmol), acetic acid (20 mg, 0.33 mmol) and sodium triacetoxyborohydride (106 mg, 0.50 mmol) were added. The reaction was stirred at room temperature over night. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (95:5 v/v) as eluent to yield the title compound (45 mg, 61%) as a yellow gum. MS ISN (m/e): 439.6 (100) [(M−H)−]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.24 (s, 1H), 7.62 (s, 1H), 7.54 (s, 1H), 7.20-7.34 (m, 5H), 7.02 (d, 1H), 6.79 (s, 1H), 6.70 (d, 1H), 4.24 (m, 1H), 3.76 (d, 1H), 3.54 (d, 1H), 3.33 (s, 3H), 3.20 (dd, 1H), 2.60 (m, 3H), 2.67 (s, 3H), 1.17 (t, 3H).

Workup

  1. additionwere added
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6a5328c5c57b48d3924b1719214f0485
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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