1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59586930, compound

HRID 1887425Notes

Reaction equation

HRID 1887425 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][NH:13][CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:16][N:17]([CH3:24])[CH2:18]/[CH:19]=[CH:20]/[C:21](O)=[O:22].CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][N:13]([C:21](=[O:22])/[CH:20]=[CH:19]/[CH2:18][N:17]([CH3:24])[CH3:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 59586841HCID 59586841, compound

Product 1

HCID 59586930HCID 59586930, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine (1000 mg, 4.0 mmol, 90% pure) in THF (20 mL) were added (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride (730 mg, 4.4 mmol), EDCI (840 mg, 4.4 mmol), DMAP (97 mmol, 0.8 mmol) and diisopropylethylamine (120 mg, 8.0 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was then concentrated to dryness under reduced pressure. The residue was purified by ISCO using a 20% ethyl acetate in methanol to obtain 1100 mg (82%) of the desired product. LCMS RT=1.51 min, [M+1]+=337.

Workup

  1. concentrationThe mixture was then concentrated to dryness under reduced pressure
  2. customThe residue was purified by ISCO

Sources & evidence

ORD record
ord-05a401a2752b4899bd3b130f450bd578
Source dataset
uspto-grants-2013_08
Patent number
US08501755B2

Reaction notes

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