Butanal → HCID 11035207, compound

HRID 2371676Notes

Reaction equation

HRID 2371676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[C:15]3[CH2:16][NH:17][CH2:18][CH2:19][C:14]=3[NH:13][C:12](=[O:20])[N:11]2[CH:21]=1.[CH:22](=O)[CH2:23][CH2:24][CH3:25].C([BH3-])#N.[Na+].Cl>O.CO>[CH2:22]([N:17]1[CH2:18][CH2:19][C:14]2[NH:13][C:12](=[O:20])[N:11]3[CH:21]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[N:9]=[C:10]3[C:15]=2[CH2:16]1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 261ButanalHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 110005642-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one

Product 1

HCID 11035207HCID 11035207, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one (171 mg, 0.6 mmol) in pH4-5 HCL-methanol (6 mL) at room temperature was added n-butyraldehyde (53 uL, 0.6 mmol) and sodium cyanoborohydride (38 mg, 0.6 mmol). After the reaction mixture was stirred for 6 hours, concentrated HCl was added until the mixture became homogenous. The mixture was then diluted with water (5 mL) and extracted twice with ether. The aqueous layer was made alkaline with aqueous ammonium hydroxide, saturated with sodium chloride, and extracted twice with 10% methanol/ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 9-n-Butyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one (Compound 48). Recrystallization from aqueous ethanol gave a white fluffy solid, m.p. 251°-253° C. (d).

Workup

  1. extractionextracted twice with ether
  2. extractionsaturated with sodium chloride, and extracted twice with 10% methanol/ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc6859870848495d955256c18e166e69
Source dataset
uspto-grants-1992_03
Patent number
US05095015

Reaction notes

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