Water → HCID 58459927, compound

HRID 2406311Notes

Reaction equation

HRID 2406311 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C(Cl)Cl.O>CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:16][CH:13]2[CH2:15][CH2:14]2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 58459927HCID 58459927, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.25 g, 5.8 mmol) in methanol (4 mL) at 0° C. was added cyclopropylamine (0.69 mL, 10 mmol). The mixture was allowed to stir at RT for 4 h. and then DCM (20 mL) and water (20 mL) were added. The mixture was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% DCM in iso-hexane) gave 2-chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (472 mg, 34%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=238 at 3.64 min. 1H NMR (400 MHz, CDCl3): δ 8.27 (d, J=1.1 Hz, 1H), 5.56 (br s, 1H), 3.03-2.93 (m, 1H), 0.99-0.89 (m, 2H), 0.65-0.60 (m, 2H).

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue via silica gel column chromatography (0-100% DCM in iso-hexane)

Sources & evidence

ORD record
ord-e3242a78d8c14a4e9795208936d75502
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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