Isopropanol → HCID 67382070, compound

HRID 910199Notes

Reaction equation

HRID 910199 reaction equation
Cl[C:2]1[C:3]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][S:10][C:4]=2[N:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(CC)CC)C.CC(O)C>O>[Cl:9][CH2:8][C:6]1[N:7]=[C:2]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:3]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][S:10][C:4]=2[N:5]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 23726818HCID 23726818, compound

Product 1

HCID 67382070HCID 67382070, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture of 4-chloro-2-chloromethyl-5-phenylthieno[2,3-d]pyrimidine (0.50 g, 1.69 mmol), 2-aminomethylpyridine (0.17 ml, 1.69 mmol), triethylamine (0.26 ml, 1.86 mmol) and propan-2-ol (15 ml) was stirred at ambient temperature for 4 days. The solution was then poured into water (150 ml) and extracted with ethyl acetate (3×75 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:4) gave (2-chloromethyl-5-phenylthieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (0.17 g), m.p. 97°-99° C.

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto give the crude product
  5. customPurification by flash chromatography (silica)
  6. washeluting with ethyl acetate and 40°-60° petroleum ether (1:4)

Sources & evidence

ORD record
ord-1f6571ee506d45bc920636b66ce7ac56
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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