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

HRID 1771931Notes

Reaction equation

HRID 1771931 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.O>C(O)C>[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 962WaterHCID 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-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-Dichloro-5-phenyl-thieno[2,3-d]pyrimidine (1.77 g, 6.3 mmol), 2-aminomethylpyridine (Aldrich, 782 μl, 7.6 mmol), and triethylamine (VWR, 1.06 ml, 7.63 mmol) were refluxed in ethanol (30 ml) for 3 hrs. On cooling, the reaction was poured into water (300 ml) and stirred for 1 hr. The resulting precipitate was filtered, washed with water (2×30 ml) and dried under vacuum at 40° C. to give (2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-pyridin-2-ylmethyl-amine as a pale-yellow solid. Yield=(1.55 g, 70%).

Workup

  1. temperatureOn cooling
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (2×30 ml)
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-0653c5f4fe4047379d2be81a255354fd
Source dataset
uspto-grants-2016_02
Patent number
US09249155B2

Reaction notes

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