Water → 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410050

Reaction equation

HRID 1410050 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][O:13][CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([N:16]3[CH2:17][CH2:18][CH2:19][CH:15]3[CH2:14][O:13][CH3:12])[CH:21]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidineHCID 683793313-(2-(Methoxymethyl)pyrrolidin-1-yl)aniline

Product 1

HCID 866717845-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amineYield 64.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (170 mg, 0.83 mmol), 3-(2-(methoxymethyl)pyrrolidin-1-yl)aniline (170 mg, 0.83 mmol) and DIEA (214 g, 1.66 mmol) in 15 mL of DMSO was stirred at room temperature overnight. 100 mL of water were added, the mixture was extracted with ethyl acetate (3×30 mL). The organic layer was washed with water (2×30 mL) and brine (30 mL), concentrated under reduced pressure to give 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 64%) as a yellow solid. LC-MS: 376 [M+H]+, tR=1.75 min.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe organic layer was washed with water (2×30 mL) and brine (30 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a91775b80fe4d359ae99ac26c5b7e9b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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