7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine → HCID 58999587, compound

HRID 1593585Notes

Reaction equation

HRID 1593585 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](Cl)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:26]1CCC2C(OC)=NC=NC=2C1)C1C=CC=CC=1>N.CO>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH2:26])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineHCID 22707063HCID 22707063, compound

Product 1

HCID 58999587HCID 58999587, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (9.83 g, 38 mmol) was dissolved in solution of NH3 in MeOH (7N, 60 mL) in a re-sealable tube. The sealed tube was heated at 100° C. for 21 h. The reaction was cooled to room temperature and kept standing at room temperature for 48 h which led to the precipitation of the desired product 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine. (5.1 g, 56%). The mother liquor was evaporated and dried under vacuum to yield a mixture of 4.12 g of desired product together with the side product 7-benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customwhich led to the precipitation of the desired product 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine
  3. customThe mother liquor was evaporated
  4. customdried under vacuum
  5. customto yield

Sources & evidence

ORD record
ord-46e2b1438fe7407ca5874e63cf62a003
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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