Triethylamine → HCID 118129690, compound

HRID 1056849Notes

Reaction equation

HRID 1056849 reaction equation
Cl[C:2]1[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]=2[N:5]=[C:6]([CH2:8][O:9][C:10](=[O:12])[CH3:11])[N:7]=1.Cl.[CH:21]1([CH2:24][NH2:25])[CH2:23]C1.[CH2:26](N(CC)CC)C>C(#N)C>[CH:24]1([N:25]([CH3:26])[C:2]2[C:3]3[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=4[S:13][C:4]=3[N:5]=[C:6]([CH2:8][O:9][C:10](=[O:12])[CH3:11])[N:7]=2)[CH2:21][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 89713563Acetic acid 4-chloro-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester

Product 1

HCID 118129690HCID 118129690, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of acetic acid 4-chloro-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester (3.5 g, 0.011 mol), cyclopropylmethylamine hydrochloride (2.5 g, 0.023 mol) and triethylamine (4.6 g, 0.046 mol) in acetonitrile (15 ml) was stirred at room temperature for 12 h. The solvent was removed by distillation, and the residue was diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over anhydrous sodium sulphate, concentrated to give acetic acid 4-(cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester (3.5 g, 89%) as brown solid. 1H NMR (400 MHz, CDCl3): δ 0.43-0.47 (m, 2H), 0.69-0.77 (m, 2H), 1.71-1.77 (m, 2H), 1.87-1.93 (m, 2H), 2.18 (s, 3H), 2.82-2.92 (m, 5H), 3.03 (s, 3H), 5.19 (s, 2H); LC-MS: [M+H]=331.8 m/z.

Workup

  1. customThe solvent was removed by distillation
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b30443409a4a4fd9b09f5da5cfeb38a4
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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