Dimethyl Sulfoxide → HCID 86694744, compound

HRID 475260Notes

Reaction equation

HRID 475260 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[CH:13]1([C:16]2[NH:20][N:19]=[C:18]([NH2:21])[CH:17]=2)[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.CS(C)=O>O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([NH:21][C:18]2[CH:17]=[C:16]([CH:13]3[CH2:15][CH2:14]3)[NH:20][N:19]=2)[N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 86694744HCID 86694744, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottom flask was charged with methyl 2,6-dichloropyrimidine-4-carboxylate (6.9 g, 33.2 mmol), 5-cyclopropyl-1H-pyrazol-3-amine (4.13 g, 33.6 mmol), DIPEA (11.6 mL) and DMSO (40 mL). The reaction was stirred at RT for 4 h then H2O (150 mL) was added. The mixture was vigorously stirred for 20 min, the resulting precipitate was filtered and washed with water, then dried under high vacuum to afford 10.87 g (>100%) of methyl 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-4-carboxylate (212): MS (ESI) m/z=294.2 [M+1]+.

Workup

  1. stirringThe mixture was vigorously stirred for 20 min
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-6c4946f9250d4ff7927a933753f15c7c
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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