Triethylamine → HCID 21912438, compound

HRID 1831653Notes

Reaction equation

HRID 1831653 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[N:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:1]([CH:3]([O:6][C:7]1[N:12]=[C:11]([CH3:13])[N:10]=[C:9]2[C:8]=1[NH:24][C:33](=[O:35])[N:14]2[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 21912081HCID 21912081, compound

Product 1

HCID 21912438HCID 21912438, compoundYield 254.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(1-ethyl-propoxy)-2-methyl-N4-(2,4,6-trimethyl-phenyl)-pyrimidine-4,5-diamine (182 mg, 0.554 mmol), triethylamine (39 mg, 0.388 mmol) and triphosgene (58 mg, 0.196 mmol) in 6 ml of dry THF was stirred at room temperature for 30 min. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 177 mg (90%) of the title compound as a white solid, mp 159–160° C. 1H NMR(CDCl3) δ 8.50(s,1H), 6.99(s,2H), 5.30(m,1H), 2.47(s,3H), 2.32(s,3H), 2.08(s,6H), 1.73(m,4H), 0.94(t,6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7a8a8aa95bb40b5b001bf1723bce917
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

Loading…