Hydrochloric Acid → 2-Methylpentane

HRID 567900Notes

Reaction equation

HRID 567900 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:23](O)=[O:24])=[C:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].[NH2:31][CH2:32][CH2:33][OH:34].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl>ClCCl>[CH3:12][CH2:10][CH2:9][CH:6]([CH3:7])[CH3:5].[OH:34][CH2:33][CH2:32][NH:31][C:23]([C:9]1[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]=2[S:11][C:10]=1[CH2:12][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][CH:22]=1)=[O:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22257999HCID 22257999, compound

Product 2

HCID 78922-MethylpentaneHCID 22257990HCID 22257990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid (50 mg) and 2-aminoethanol (14 μl ) in dichloromethane (2 ml) was added 1-hydroxybenzotriazole hydrate (48 mg) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (45 mg). The reaction mixture was stirred at room temperature for 18 hours then hydrochloric acid (1M, 20 ml) was added and the mixture was extracted with ether (30 ml). The organic extracts were washed with water, then with 1M sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate: isohexane to give the title compound (28 mg).

Workup

  1. extractionthe mixture was extracted with ether (30 ml)
  2. washThe organic extracts were washed with water
  3. dry with materialwith 1M sodium hydroxide solution, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0f6cf88882da424491bef1691608d4f6
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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