Triethylamine → HCID 21912438, compound

HRID 967978Notes

Reaction equation

HRID 967978 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-870d5cba9da3412fab7cc44752ccd74c
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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