Triethylamine → HCID 58441956, compound

HRID 552109Notes

Reaction equation

HRID 552109 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][CH2:28][NH2:29].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>C1COCC1.O.CCOC(C)=O>[CH:9]1([NH:8][C:6]2[C:5]([NH2:12])=[CH:4][N:3]=[C:2]([NH:29][CH2:28][CH2:27][C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)[N:7]=2)[CH2:11][CH2:10]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 24489Sodium DithioniteHCID 116521ThiopheneethanamineHCID 516892Sodium BicarbonateHCID 24903951HCID 24903951, compound

Product 1

HCID 58441956HCID 58441956, compoundYield 62.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.2 g (0.93 mmol, 1.0 eq.) of 2-chloro-N-cyclopropyl-5-nitropyrimidin-4-amine (I-1) in 5 mL of THF was added 0.19 mL (1.4 mmol, 1.5 eq.) of triethylamine followed by 0.14 g (1.1 mmol, 1.2 eq.) of 2-thiophene ethylamine. The reaction mixture was stirred at room temperature for 30 min and 2 mL of THF was added. A solution of 1.0 g (˜5.7 mmol, ˜85% tech. grade, ˜6.0 eq.) of sodium hydrosulfite and 1.0 g (12 mmol, ˜13 eq.) of sodium hydrogen carbonate in 10 mL of water was added, and the mixture was stirred vigorously at room temperature for 1 h. The mixture was diluted with 20 mL of EtOAc and washed 10 mL of sat. brine. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo to provide 0.16 g of crude N4-cyclopropyl-N2-(2-(thiophen-2-yl)ethyl)pyrimidine-2,4,5-triamine (I-3).

Workup

  1. stirringthe mixture was stirred vigorously at room temperature for 1 h
  2. washwashed 10 mL of sat. brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-149e8ce701a4494aa6d578d477b92476
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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