HCID 22102662, compound → HCID 178484442, compound

HRID 1456956Notes

Reaction equation

HRID 1456956 reaction equation
[CH2:1]([O:8][C:9]1[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][C:10]=1[O:11][C:12]1[N:17]=[C:16]([NH:18][CH2:19][C:20]([O:22]CC)=O)[C:15]([N+:25]([O-])=O)=[C:14]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH:30]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Zn].O1CCCC1>[CH2:1]([O:8][C:9]1[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][C:10]=1[O:11][C:12]1[NH:17][C:16]2[C:15](=[C:14]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH:30]=3)[N:13]=1)[NH:25][C:20](=[O:22])[CH2:19][N:18]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22102662HCID 22102662, compound

Product 1

HCID 178484442HCID 178484442, compoundYield 139.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2-(2-Benzyloxy-5-cyanophenoxy)-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(3-(dimethylaminocarbonyl)phenoxy)pyrimidine (1.1 g, 1.80 mmol), a compound of formula (H), and granular zinc (0.5 g) were mixed with tetrahydrofuran (50 mL) and 10% aqueous HCI (10 mL). The reaction mixture was heated for 30 minutes at 70° C. The volatiles were evaporated. Saturated aqueous NaHCO3 was added and the solution extracted with ethyl acetate (300 mL). The organic layer was dried (Na2SO4) and evaporated to afford 1.35 g of 2-(2-benzyloxy-5-cyanophenoxy)-4-(3-(dimethylaminocarbonyl)phenoxy)-1,7-dihydro-6(5H)-pteridinone, a compound of formula (J).

Workup

  1. customThe volatiles were evaporated
  2. additionSaturated aqueous NaHCO3 was added
  3. extractionthe solution extracted with ethyl acetate (300 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-261af16e10e74b87a86be581c62c4855
Source dataset
uspto-grants-1998_12
Patent number
US05846972

Reaction notes

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