Diisopropylethylamine → HCID 11950624, compound

HRID 2243754Notes

Reaction equation

HRID 2243754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22](O)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31].[CH:32]([N:35](C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([NH:35][CH3:32])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 119506223-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid

Product 1

HCID 11950624HCID 11950624, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (0.59 g, 1.33 mmol) was taken up in CH2Cl2 (75 mL), and diisopropylethylamine (0.7 mL, 4 mmol) was added followed by HATU (0.556 g, 1.46 mmol). Gaseous methyl amine was then bubbled in very slowly until reaction was complete. Aqueous workup followed by chromatography on silica gel (100 g) eluted with CH2Cl2 —90% EtOAc/CH2Cl2 gave the title compound as a white amorphous solid. mp 273-275° C. LC-MS m/z 456 (M+H)+, 1.85 min (ret time).

Workup

  1. customGaseous methyl amine was then bubbled in
  2. customvery slowly until reaction
  3. washeluted with CH2Cl2 —90% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8c3782dada454e8bbc883b47152905a5
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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