Water → HCID 22258048, compound

HRID 567912Notes

Reaction equation

HRID 567912 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]=2[S:8][C:7]=1[CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41].O>ClCCl>[CH3:16][N:12]1[C:13](=[O:15])[C:14]2[C:6]([S:5][CH2:4][CH2:3][CH2:2][NH:1][C:40](=[O:42])[CH3:41])=[C:7]([CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[S:8][C:9]=2[N:10]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:11]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22257960HCID 22257960, compound

Product 1

HCID 22258048HCID 22258048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[(3-Aminopropyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (51 mg) and triethylamine (100 μl) were dissolved in dichloromethane (2 ml) and acetyl chloride (25 μl) was added. The reaction was stirred overnight, then water was added and the phases were separated. The aqueous phase was extracted with dichloromethane, then the organic phases were combined, dried, filtered and evaporated. Purification by HPLC (ethanol:dichloromethane 1-10: 99-90) gave the title compound (36 mg).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by HPLC (ethanol:dichloromethane 1-10: 99-90)

Sources & evidence

ORD record
ord-255d83b5206945b1848c756d5bbd653b
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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