Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2382106Generated: November 2, 2026

Diisopropylethylamine → HCID 59199979, compound

https://huagongshe.com/reaction/2382106

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantSodium BicarbonateHCID 516892—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant4-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 61702025—
ReactantHCID 68552172HCID 68552172—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 59199979HCID 5919997917.4%

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of 3-methyl-pyrrolo[3,2-c]pyridin-1-yl amine (223 mg, 1.52 mmol), 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (329 mg, 1.52 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is stirred at 150° C. for 1 h. The reaction is quenched with water and NaHCO3 (168 mg, 2 mmol). The mixture is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% meOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide (91 mg, 17%). MS: 345 (M+H); 1H NMR (300 MHz, DMSO-d6): δ=9.34 (s, 2H), 8.79 (d, 1H), 8.53 (d, 1H), 8.45 (d, 1H), 8.13 (d, 1H), 8.02 (t, 1H), 7.86 (s, 1H), 7.59 (t, 1H), 2.77 (s, 3H), 2.43 (s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08258130B2
Source datasetuspto-grants-2012_09
ORD IDord-b20b7f893ad64bb18f8dad39ae733102
Source noteuspto-grants-2012_09