Triethylamine → 2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1910453Notes

Reaction equation

HRID 1910453 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:12])[C:5]2[S:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1.[CH:13]1[C:18]2[CH2:19][NH:20][CH2:21][CH2:22][S:23](=[O:24])[C:17]=2[CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:24]=[S:23]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:18]=2[CH2:19][N:20]([C:2]2[NH:3][C:4](=[O:12])[C:5]3[S:10][C:9]([CH3:11])=[CH:8][C:6]=3[N:7]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 1363597872-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 1363597882-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4(3H)-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (3.01 g, 15 mmol) was dissolved in toluene (50 mL), followed by addition of 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene-5-oxide (3.39 g, 18.7 mmol), triethylamine (6 mL, 43 mmol). Then the solution was heated to reflux overnight. The suspension was filtrated and the solid was washed by methanol to afford 4.2 g of 2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 81.1%) as a slight brown solid. MS obsd. (ESI+) [(M+H)+] 346.

Workup

  1. temperatureThen the solution was heated
  2. temperatureto reflux overnight
  3. filtrationThe suspension was filtrated
  4. washthe solid was washed by methanol

Sources & evidence

ORD record
ord-546760932c7d4ce7851aa7b19caadd55
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

Loading…