Dimethylamine → HCID 14788029, compound

HRID 1722398Notes

Reaction equation

HRID 1722398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[NH:12][C:13]([CH3:31])=[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=2)=[CH:5][CH:4]=1.[N:32]1[CH:37]=CC=C[CH:33]=1.[C:38](Cl)(Cl)=[O:39].CNC>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[N:16]([C:38]([N:32]([CH3:37])[CH3:33])=[O:39])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:13]([CH3:31])[N:12]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 6371PhosgeneHCID 13885858HCID 13885858, compound

Product 1

HCID 14788029HCID 14788029, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.5 g, 1.1 mmole) in 10 ml of dry tetrahydrofuran under argon at 0°-5° C. was treated with pyridine (1.0 ml, 12.6 mmole), then with phosgene (1.16 ml of 12.5% in benzene, 1.47 mmol). After 0.5 hours at 0°-5° C., dimethylamine (1 ml of 40% aqueous, excess) was added. Reaction was complete within 0.5 hours. The mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, water and saturated brine. The aqueous washes were back extracted with fresh ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give 0.6 g of essentially homogeneous product.

Workup

  1. customReaction
  2. waitwas complete within 0.5 hours
  3. washwashed with 1N hydrochloric acid, water and saturated brine
  4. extractionThe aqueous washes were back extracted with fresh ethyl acetate
  5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give 0.6 g of essentially homogeneous product

Sources & evidence

ORD record
ord-5cc4b60efcc7406eb2e4e975840d0815
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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