Triethylamine → HCID 22258034, compound

HRID 567910Notes

Reaction equation

HRID 567910 reaction equation
[OH: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.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:40][S:41]([O: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]([CH3:20])[CH3:21])[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)(=[O:43])=[O:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 52825395-[(3-Hydroxypropyl)sulfanyl]-1-isobutyl-3-methyl-6-(1-naphthylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 22258034HCID 22258034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5- [(3-Hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Example 4) (403 mg) was dissolved in dichloromethane (6 ml). Triethylamine (300 μl) was added followed by methanesulfonyl chloride (150 μl ) and the mixture was stirred overnight. Sodium bicarbonate (aqueous) was added and the phases were separated. The aqueous phase was extracted twice with dichloromethane, the organic phases were combined, washed with brine, dried, filtered and evaporated to give the subtitle compound (0.57 g).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-90295f2a60504f50bd321905a55d068c
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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