Tetrahydrofuran → HCID 20284789, compound

HRID 127520

Reaction equation

HRID 127520 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[C:16]2C3C(=CC=CC=3)N[C:8]=2[S:7]CC1.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.[C:24]([O:28][C:29](SC1N=C(C)C=C(C)N=1)=[O:30])([CH3:27])([CH3:26])[CH3:25].O1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[C:24]([O:28][C:29]([N:2]([CH2:3][CH:4]1[C:23]2[C:21]3[C:20](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:19][C:22]=2[S:7][CH2:8][CH2:16]1)[CH3:1])=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioateHCID 30560964-Methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Product 1

HCID 20284789HCID 20284789, compoundYield 93%

Procedure

To a solution of 4-methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (4.41 g) in tetrahydrofuran (50 ml) are added triethylamine (4 ml) and 2-(t-butoxycarbonylthio)-4,6-dimethylpyrimidine (4.76 l g) successively at room temperature. The mixture is stirred at room temperature for 2.5 hours and evaporated to remove the solvent. The residue is extracted with chloroform after addition of water. The extract is washed, dried and evaporated to give crude crystals. Recrystallization from acetone gives the title compound (5.57 g) melting at 220°-222° C. (decomp.).

Workup

  1. customevaporated
  2. customto remove the solvent
  3. extractionThe residue is extracted with chloroform
  4. additionafter addition of water
  5. washThe extract is washed
  6. customdried
  7. customevaporated
  8. customto give crude crystals
  9. customRecrystallization from acetone

Sources & evidence

ORD record
ord-769f2ca02fde48049ef46625e6e97232
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Linked notes

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