3-amino-N,N-dimethylpropane-1-sulfonamide → 3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-amino]-propane-1-sulfonic acid dimethylamide

HRID 2262270Notes

Reaction equation

HRID 2262270 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:19][N:20]([CH3:28])[S:21]([CH2:24][CH2:25][CH2:26][NH2:27])(=[O:23])=[O:22]>CO.C(O)C.[Pd]>[CH3:19][N:20]([CH3:28])[S:21]([CH2:24][CH2:25][CH2:26][NH:27][CH2:11][C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[CH:8]=1)(=[O:23])=[O:22]

Participants

6

Reactant 2

HCID 192616433-amino-N,N-dimethylpropane-1-sulfonamideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 866184503-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-amino]-propane-1-sulfonic acid dimethylamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (280 mg) in methanol (10 mL) was added 3-amino-propane-1-sulfonic acid dimethylamide (284 mg) and the reaction stirred at room temperature for 16 h. The solvent was reduced in vacuo and the residue redissolved in ethanol (50 mL). Palladium on carbon (20 mg) was added and the reaction stirred at room temperature under a hydrogen balloon for 48 h. The reaction was then filtered through Celite and the filtrate reduced in vacuo to give 3-[(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-amino]-propane-1-sulfonic acid dimethylamide as a yellow solid.

Workup

  1. stirringthe reaction stirred at room temperature under a hydrogen balloon for 48 h
  2. filtrationThe reaction was then filtered through Celite

Sources & evidence

ORD record
ord-8442ba2d0af248f78022ba0218080197
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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