Triethylamine → HCID 11761005, compound

HRID 1728557Notes

Reaction equation

HRID 1728557 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:18]=[C:19]2[C:24]3[CH2:25][NH:26][CH2:27][CH2:28][C:23]=3[NH:22][C:21](=[O:29])[N:20]2[CH:30]=1.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:26]1[CH2:27][CH2:28][C:23]2[NH:22][C:21](=[O:29])[N:20]3[CH:30]=[C:17]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[F:10])[N:18]=[C:19]3[C:24]=2[CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67968alpha-Bromo-o-fluorotolueneHCID 110005642-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one

Product 1

HCID 11761005HCID 11761005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluorobenzyl bromide (54 uL, 0.45 mmol) was added to a solution of 2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one (128 mg, 0.45 mmol) and triethylamine (76 uL, 0.54 mmol) in DMF (1 mL) at room temperature. The reaction mixture was stirred for 45 minutes, and then concentrated. Aqueous sodium bicarbonate was added, the aqueous layer extracted twice with 10% methanol/ethyl acetate, and the combined organic layers dried over magnesium sulfate, filtered, concentrated, and triturated with methanol/ether to give 9-(2-Fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one (Compound 13) as an off-white solid, m.p. 270°-273° C. Treatment with ethanolic HCl affords the corresponding HCl salt.

Workup

  1. concentrationconcentrated
  2. additionAqueous sodium bicarbonate was added
  3. extractionthe aqueous layer extracted twice with 10% methanol/ethyl acetate
  4. dry with materialthe combined organic layers dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customtriturated with methanol/ether

Sources & evidence

ORD record
ord-fcaf8ce194974f5199390f1b12c99ce4
Source dataset
uspto-grants-1994_07
Patent number
US05328912

Reaction notes

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