Cyclopropanemethanamine → N2-Cyclopropylmethyl-5-phenyl-N4-pyridin-2-ylmethyl-thieno[2,3-d]pyrimidine-2,4-diamine

HRID 910189Notes

Reaction equation

HRID 910189 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=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.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1>O>[CH:25]1([CH2:28][NH:29][C:2]2[N:3]=[C:4]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][S:8][C:6]=3[N:7]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 865963692-chloro-5-phenyl-N-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 86596370N2-Cyclopropylmethyl-5-phenyl-N4-pyridin-2-ylmethyl-thieno[2,3-d]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10 ml glass tube were placed 2-chloro-N-(2-pyridyl)methyl-5-phenylthieno[2,3-d]pyrimidin-4-ylamine (0.03 g, 0.0852 mmol) and cyclopropylmethylamine (0.5 ml). The vessel was sealed with a septum and placed in the microwave cavity. Microwave irradiation of 200 W was used, the temperature being ramped from room temperature to 200° C. Once 200° C. was reached, the reaction mixture was held at this temperature for 40 minutes. After cooling to ambient temperature, water (4 ml) was added and the mixture stirred for 2.5 hours. The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give N2-Cyclopropylmethyl-5-phenyl-N4-pyridin-2-ylmethyl-thieno[2,3-d]pyrimidine-2,4-diamine (0.025 g) as a yellow solid, m.p.t. 109-111° C.

Workup

  1. customIn a 10 ml glass tube were placed
  2. customThe vessel was sealed with a septum
  3. customMicrowave irradiation of 200 W
  4. custombeing ramped from room temperature to 200° C
  5. customOnce 200° C.
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-1868b65da0814ef582aa307f1c52a5ea
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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