Acetic Acid → HCID 57802999, compound

HRID 2102365Notes

Reaction equation

HRID 2102365 reaction equation
[C:1]1([C:7]2[C:15]3[C:14]([NH:16][CH2:17][CH2:18][NH2:19])=[N:13][CH:12]=[N:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)([O-:22])=[O:21].C(O)(=O)C.[BH4-].[Na+]>C(OCC)(=O)C.O.C(O)C>[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH:19][CH2:18][CH2:17][NH:16][C:14]1[C:15]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][S:9][C:10]=2[N:11]=[CH:12][N:13]=1)([O-:22])=[O:21]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 2796098HCID 2796098, compoundHCID 4311764Sodium borohydride

Product 1

HCID 57802999HCID 57802999, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(5-phenylthieno[2,3-d]pyrimidin-4-yl)ethane-1,2-diamine (Maybridge) (30 mg, 0.11 mmol), 3-nitrobenzaldehyde (18 mg, 0.12 mmol), acetic acid (6 mg, 0.10 mmol) and ethanol (3.0 mL) was stirred at room temperature for 30 minutes, followed by the addition of 7.6 mg (0.20 mmol) of sodium borohydride (7.6 mg, 0.20 mmol). The reaction was stirred for an additional 30 minutes and then water (0.2 mL) and ethyl acetate (20 mL) were added. The mixture was washed with aqueous sodium bicarbonate solution (2×20 mL) and the organic layer was separated, concentrated, and purified by column chromatography over silica gel using a gradient elution from 2.5% to 5% methanol in dichloromethane as eluant to give 34.2 mg (77%) N-(3-nitrobenzyl)-N′-(5-phenylthieno[2,3-d]pyrimidin-4-yl)ethane-1,2-diamine as a colorless gum. MS [M+H] 406.2, 1H NMR (CDCl3) δ (ppm) 8.49 (s, 1H), 8.11 (d, J=6.6 Hz, 1H), 8.06 (s, 1H), 7.50-7.32 (m, 7H), 7.08 (s, 1H), 5.48 (b, 1H), 3.75 (s, 2H), 3.55 (m, 2H), 2.75 (m, 2H).

Workup

  1. stirringThe reaction was stirred for an additional 30 minutes
  2. washThe mixture was washed with aqueous sodium bicarbonate solution (2×20 mL)
  3. customthe organic layer was separated
  4. concentrationconcentrated
  5. custompurified by column chromatography over silica gel using
  6. washa gradient elution from 2.5% to 5% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-fd85db4d08bd4b20a5187df24ff31613
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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