2-Methylpentane → 3-Chloro-5-(10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)benzonitrile

HRID 2201173Notes

Reaction equation

HRID 2201173 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]2[N:11]([CH2:23][CH2:24][S:25]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:12]=[C:13]3[C:18]=2[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]3[CH3:22])[CH:9]=1)[C:5]#[N:6].[Cl:45][C:46]1[O:50][C:49]([CH:51]=O)=[CH:48][CH:47]=1.[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.CCCC(C)C>C1(C)C=CC=CC=1.CO.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]2[N:11]3[C:12]([CH:51]([C:49]4[O:50][C:46]([Cl:45])=[CH:47][CH:48]=4)[S:25][CH2:24][CH2:23]3)=[C:13]3[N:14]([CH3:22])[C:15](=[O:21])[N:16]([CH3:20])[C:17](=[O:19])[C:18]=23)[CH:9]=1)[C:5]#[N:6]

Participants

8

Reactant 4

HCID 78922-MethylpentaneHCID 27696305-Chloro-2-furaldehydeHCID 9917655Bi(OTf)3HCID 867235243-Chloro-5-(1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Product 1

HCID 771056013-Chloro-5-(10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)benzonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

3-Chloro-5-(1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (Intermediate GA) (146 mg, 0.237 mmol), 5-chlorofuran-2-carbaldehyde (34.0 mg, 0.260 mmol) and bismuth (III) triflate (31.0 mg, 0.047 mmol) were suspended in toluene (Volume: 2.5 ml). The reaction was then heated to 100° C. under microwave irradiation for 3 hr. The reaction mixture was suspended in MeOH (50 mL) and adsorbed onto silica. The residue was purified via ISCO SiO2 12 g Redisep Rf column eluting with 20% EtOAc/hexane. Fractions were combined and evaporated to afford a pale yellow gum. The gum was dissolved in Et2O (30 mL) and iso-hexane (30 mL) was added to afford a suspension. The solvent was evaporated to afford the title compound as a pale yellow solid.

Workup

  1. customThe residue was purified via ISCO SiO2 12 g Redisep Rf column
  2. washeluting with 20% EtOAc/hexane
  3. customevaporated
  4. customto afford a pale yellow gum
  5. customto afford a suspension
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2a530c970469446080bb5909bf36ea09
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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