2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde → HCID 86638093, compound

HRID 2365191Notes

Reaction equation

HRID 2365191 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:16][O:17][CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:26][C:27]1[N:28]=[C:29]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[C:30]2[S:35][C:34](C=O)=[CH:33][C:31]=2[N:32]=1>>[CH2:19]([N:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:6][C:34]2[S:35][C:30]3[C:29]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:28][C:27]([Cl:26])=[N:32][C:31]=3[CH:33]=2)[CH2:13][CH2:12]1)[CH2:15][CH2:16][O:17][CH3:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 68715963HCID 68715963, compound

Product 1

HCID 86638093HCID 86638093, compoundYield 69.5%

Procedure

The reaction mixture was cooled and diluted with dichloromethane (30 ml), washed with water, brine and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by silica flash chromatography to give 4-[benzyl-(2-methoxy-ethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (484 mg). 4-[Benzyl-(2-methoxy-ethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (442 mg), and 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (300 mg) were treated under standard reductive amination conditions to give benzyl-[1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-ylmethyl)-piperidin-4-yl]-(2-methoxy-ethyl)-amine (379 mg), as an oil which crystallized on standing.

Sources & evidence

ORD record
ord-959f2061b39b4708b2045412d077d947
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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