Isopropanol → 2-chloro-5-phenyl-N-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine

HRID 910188Notes

Reaction equation

HRID 910188 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(N(CC)CC)C.CC(O)C>O>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

Product 1

HCID 865963692-chloro-5-phenyl-N-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amineYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine (0.82 g, 2.92 mmol), 2-(aminomethyl)pyridine (0.35 g, 3.21 mmol), triethylamine (0.32 g, 0.45 ml, 3.21 mmol) and propan-2-ol (20 ml) was stirred at ambient temperature for 72 hours. Water (50 ml) was added to the reaction mixture and the organic phase was extracted using dichloromethane (3×50 ml). The combined extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give 2-chloro-N-(2-pyridyl)methyl-5-phenylthieno[2,3-d]pyrimidin-4-ylamine (1.0 g) as a white solid which was used without further purification.

Workup

  1. extractionthe organic phase was extracted
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a918ccac91634ac1a3b5a626c575839e
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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