Cyclopropanemethanamine → [1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-cyclopropylmethyl-amine

HRID 2066469Notes

Reaction equation

HRID 2066469 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([NH:29][CH2:28][CH:25]4[CH2:27][CH2:26]4)[CH2:16][CH2:17]3)=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 75646CyclopropanemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 581171371-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-one

Product 1

HCID 58117134[1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-cyclopropylmethyl-amineYield 44%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-one (0.2 g, 0.545 mmol) in 1,2-dichloroethane (3 mL) were added cyclopropanemethylamine (71 μL, 0.812 mmol) and sodium triacetoxyborohydride (0.15 g, 0.71 mmol). The resulting suspension was stirred at RT for 17 h, then diluted with water and DCM. The aqueous layer was separated and extracted with DCM. The combined organic layers were dried (Na2SO4), then concentrated in vacuo to give the title compound as an off-white solid (0.10 g, 44%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bbc0dfa93a84119a82307ba213ae48b
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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