Hydrochloric Acid → 5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine

HRID 1677262Notes

Reaction equation

HRID 1677262 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][C:16](=[CH:19]COC)[C:17]#[N:18])([CH3:3])[CH3:2].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].C[O-].[Na+].Cl>C(O)C.C(OCC)C>[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][C:16]1[C:17]([NH2:18])=[N:29][C:28]([NH2:30])=[N:27][CH:19]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium MethoxideHCID 670534062-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile

Product 1

HCID 161192135-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine was prepared from 2-(6-isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile by treatment with guanidine carbonate and sodium methoxide using the procedure of step 7 of Example 2 above. This material was dissolved in 2.5 ml absolute ethanol, and 820 ml of 1 N HCl in diethyl ether was added with stirring. Diethyl ether was added slowly until small crystals formed, and the solution was then placed in a −10 C freezer for 18 hours. The solid that had formed was collected by filtration, washed with diethyl ether, and dried under vacuum at 45 C. to give 171 mg. of the hydrochloride salt, Mp: 185.1° C.

Workup

  1. customformed
  2. customThe solid that had formed
  3. filtrationwas collected by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum at 45 C
  6. customto give 171 mg

Sources & evidence

ORD record
ord-b701dc3b68fc4d70bd9b83a33c93b0df
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

Loading…