Methyl iodide → 5-[2-Isobutoxy-5-(methylsulfanyl)-3-pyridinyl]-2-methyl-3-propyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354209

反応式

HRID 354209 の反応式
I[C:2]1[CH:3]=[C:4]([C:13]2[NH:14][C:15](=[O:26])[C:16]3[C:17](=[C:19]([CH2:23][CH2:24][CH3:25])[N:20]([CH3:22])[N:21]=3)[N:18]=2)[C:5]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[N:6][CH:7]=1.N[C:28](N)=[S:29].C([BH3-])#N.[Na+].[O-2].[Ca+2].CI>CN(C)C=O.C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CC[PH+](CC)CC.CC[PH+](CC)CC.Cl[Ni]Cl>[CH2:9]([O:8][C:5]1[C:4]([C:13]2[NH:14][C:15](=[O:26])[C:16]3[C:17](=[C:19]([CH2:23][CH2:24][CH3:25])[N:20]([CH3:22])[N:21]=3)[N:18]=2)=[CH:3][C:2]([S:29][CH3:28])=[CH:7][N:6]=1)[CH:10]([CH3:12])[CH3:11]

参加物

10

反応物 5

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 5003444Sodium cyanoborohydride2 回HCID 6850728CalciumoxideHCID 1357305795-(5-Iodo-2-isobutoxy-3-pyridinyl)-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

生成物 1

HCID 1357305875-[2-Isobutoxy-5-(methylsulfanyl)-3-pyridinyl]-2-methyl-3-propyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

試薬・触媒・溶媒 4

HCID 6329432Dichloronickel;bis(triethylphosphanium)触媒2 回HCID 311Citric Acid溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The title compound of example 141 (500 mg, 1.07 mmol) and thiourea (90 mg, 1.18 mmol) were suspended in N,N-dimethylformamide (3 ml), degassed at 70° C., and treated with bis(triethylphosphine)nickel(II) chloride (20 mg, 0.05 mmol). Sodium cyanoborohydride (80 μl of 1M solution in THF, 0.08 mmol) was added, and the resultant black reaction mixture heated for ¾ h before further bis(triethylphosphine)nickel(II) chloride (60 mg, 0.16 mmol) and sodium cyanoborohydride (160 μl of 1M solution in THF, 0.16 mmol) were added and the reaction mixture heated for a further 6 h. The green reaction mixture was allowed to cool to room temperature and calcium oxide (90 mg, 1.6 mmol) added. After 1 h, methyl iodide (150 ?l, 2.4 mmol) was added and the mixture stirred for a further 1 h. The reaction mixture was diluted with ethyl acetate (20 ml) and citric acid (10% aq, 20 ml), the organic phase separated and washed with further citric acid (2×20 ml), brine (20 ml) and dried (MgSO4) to afford crude 5-[2-isobutoxy-5-(methylsulfanyl)-3-pyridinyl]-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one.

後処理

  1. customdegassed at 70° C.
  2. customthe resultant black reaction mixture
  3. additionwere added
  4. temperaturethe reaction mixture heated for a further 6 h
  5. customthe organic phase separated
  6. washwashed with further citric acid (2×20 ml), brine (20 ml)
  7. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-8ba913416daf4781818b98ba41235dd1
出典データセット
uspto-grants-2004_06
特許番号
US06756373B1

関連ノート

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