Acetic Acid → N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

HRID 31860Notes

Reaction equation

HRID 31860 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14](C=O)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:10]=1.[C:28]([BH3-])#[N:29].[Na+].C(O)(=O)C.O.[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:28][N:29]2[CH2:37][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[N:10]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 22142985n-(2-{[4-(2,4-Dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide

Product 1

HCID 22142523N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

Conditions

Temperature
70 °C

Procedure

N-(2-{[4-(2,4-dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide (50 mg, 0.121 mmol) was dissolved in 5 mL of THF, 242 μL of sodium cyanoborohydride (1M in THF) and 5 μL of glacial acetic acid added and the mixture was heated to 70° C. for 18 h. Following slow addition of 1 mL of water to decompose excess reagent, the mixture was partitioned between ethyl acetate and saturated citric acid solution. The organic layer was discarded, and aqueous layer was carefully basified with sodium hydoxide to PH 9, then extracted with ethyl acetate twice. The combined organic layers was dried (sodium sulfate), concentrated, and purified by chromatography (selica gel, 10% methanol/methylene chloride) to afford N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide, 30 mg (52%).

Workup

  1. customthe mixture was partitioned between ethyl acetate and saturated citric acid solution
  2. extractionextracted with ethyl acetate twice
  3. dry with materialThe combined organic layers was dried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by chromatography (selica gel, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-8cb88e52354f4b3ea0d7f9bc8b783569
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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