2,4-Dichloropyrimidine → HCID 178478345, compound

HRID 2409000Notes

Reaction equation

HRID 2409000 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([C:12]2[CH:16]=[C:15]([NH2:17])[NH:14][N:13]=2)[CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C:15]2[NH:14][N:13]=[C:12]([CH:9]3[CH2:11][CH2:10]3)[CH:16]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 178507266HCID 178507266, compound

Product 1

HCID 178478345HCID 178478345, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A dried 5-L, three-necked round bottom flask fitted with an overhead stirrer and reflux condenser was charged with a solution of 2,4-dichloropyrimidine (250 g, 1.68 mol) in anhydrous DMSO (2300 mL). 3-Cyclopropyl-1H-pyrazol-5-amine (227.4 g, 1.85 mol) and DIPEA (438 mL, 2.52 mol) were added sequentially at RT. The resulting solution was stirred at 60° C. for 16 h, cooled to RT, and poured into ice water. The precipitated yellow solid was collected by vacuum filtration, washed with water, 1.5 N HCl (3×1 L), and finally with water (4×500 mL). The precipitate was dried by air suction overnight to give 320 g (81%) of 20 as yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 12.19 (s, 1H), 10.29 (s, 1H), 8.15 (s, 1H), 7.0 (br s, 1H), 6.0 (br s, 1H), 1.85-1.92 (m, 1H), 0.91-0.95 (m, 2H), 0.7 (m, 2H); MS (ESI+) m/z: 236 [M+1]+.

Workup

  1. temperaturereflux condenser
  2. temperaturecooled to RT
  3. filtrationThe precipitated yellow solid was collected by vacuum filtration
  4. washwashed with water, 1.5 N HCl (3×1 L)
  5. customThe precipitate was dried by air suction overnight

Sources & evidence

ORD record
ord-94c8604e9c774cb6b1e8e729a2aedbc1
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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