Hydrochloric Acid → HCID 178484442, compound

HRID 1456948Notes

Reaction equation

HRID 1456948 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.Cl>[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 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 HCl (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. customevaporated

Sources & evidence

ORD record
ord-814661d74bb247dba04b82e38a0b98c8
Source dataset
uspto-grants-1998_12
Patent number
US05846970

Reaction notes

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