tert-Butyl-2-[(3,4,5-trimethoxyphenyl)amino]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-carboxylate → N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 930492Notes

Reaction equation

HRID 930492 reaction equation
C(OC([N:8]1[CH2:30][CH2:29][C:11]2[N:12]=[C:13]([NH:16][C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[N:14]=[CH:15][C:10]=2[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:28][O:27][C:19]1[CH:18]=[C:17]([NH:16][C:13]2[N:14]=[CH:15][C:10]3[CH2:9][NH:8][CH2:30][CH2:29][C:11]=3[N:12]=2)[CH:22]=[C:21]([O:23][CH3:24])[C:20]=1[O:25][CH3:26]

Participants

4

Reactant 1

HCID 118970889tert-Butyl-2-[(3,4,5-trimethoxyphenyl)amino]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-carboxylate

Product 1

HCID 118970894N-(3,4,5-Trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-Butyl-2-[(3,4,5-trimethoxyphenyl)amino]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-carboxylate, Intermediate 2 (870 mg, 2.09 mmol) in 4.0 N HCl solution in 1,4-dioxane (15 mL) was stirred at room temperature for 20 hours (orange colored solution with precipitate). The solvent was removed in vacuo and the salt was mostly taken up in water (20 mL). The pH of the aqueous mixture was made basic by addition of 1.0 N NaOH(aq) and the white, amorphous precipitate was collected, washed with water, ethyl acetate, and dried (616 mg, 93%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe pH of the aqueous mixture was made basic by addition of 1.0 N NaOH(aq)
  3. customthe white, amorphous precipitate was collected
  4. washwashed with water, ethyl acetate
  5. customdried (616 mg, 93%)

Sources & evidence

ORD record
ord-3379bc329533442c88d74fb27beb88ad
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

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