Triethylamine → HCID 21995275, compound

HRID 1977688Notes

Reaction equation

HRID 1977688 reaction equation
N1[CH:6]=[CH:5][C:4]([C:7](N)=O)=NC=1.Cl.[C:11]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)[N:15]=1)([OH:13])=O.[CH2:33](N(CC)CC)[CH3:34].C(OC(Cl)=O)C(C)C.Cl.CNOC>C(Cl)Cl>[C:11]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)[N:15]=1)(=[O:13])[C:4]1[CH:7]=[CH:34][CH:33]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 17861762Pyrimidine-4-carboxamideHCID 21995260HCID 21995260, compound

Product 1

HCID 21995275HCID 21995275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The pyrimidine-4-carboxamide used as starting material was prepared by treating a solution of 4-carboxy-N-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine hydrochloride (2.0 g, 5.86 mmol) and triethylamine (2.0 ml, 14.0 mmol) in CH2Cl2 (40 ml), cooled to −20° under a nitrogen atmosphere, with isobutylchloroformate (1.1 ml, 7.0 mmol). The resulting mixture was stirred for 20 min. before N,O-dimethylhydroxylamine hydrochloride (683 mg, 7.0 mmol) and triethylamine (1.0 ml, 7.0 mmol) were added and the reaction allowed to warm to room temperature over 3 h. After washing with 2M hydrochloric acid (1×50 ml) and 2M NaOH solution (1×50 ml), the reaction was dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to column chromatography [silica ethyl acetate] to give the desired product (1.02 g), as a yellow oil. δH (CDCl3) 8.51 (1H, d, J 4.9 Hz), 7.21 (1H, br s), 6.92 (3H, br s), 3.86 (6H, s), 3.82 (3H, s), 3.69 (3H, br s) and 3.36 (3H, s). MS m/z 349 (M+H)+.

Workup

  1. customwas prepared
  2. additionwere added
  3. washAfter washing with 2M hydrochloric acid (1×50 ml) and 2M NaOH solution (1×50 ml)
  4. dry with materialthe reaction was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2ff6cf388054ac2866bd5507f0fb397
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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