Diisopropylethylamine → (2R)-2-{[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl](methyl)amino}pentan-1-ol

HRID 1694549Notes

Reaction equation

[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:29][NH:30][C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:32][OH:33]>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([N:30]([CH3:29])[C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:32][OH:33])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (6.0 g, 19.4 mmol) was dissolved in NMP (25 mL). DIPEA (6.8 mL, 38.8 mmol) and (2R)-2-(methylamino)pentan-1-ol (3.4 g, 29.1 mmol) were added and the mixture was heated to 120° C. for 3 days. Additional (2R)-2-(methylamino)pentan-1-ol (350 mg, 2.99 mmol) and DIPEA (1 mL, 5.74 mmol) was added and the reaction mixture was heated for 6 h at 120° C. After cooling to room temperature, the mixture was poured into ice. The precipitated product was collected by filtration and purified by flash column chromatography (eluent DCM:ethyl acetate gradient) to yield the title compound (5.74 g, 76% yield).

Workup

temperaturethe reaction mixture was heated for 6 h at 120° C
temperatureAfter cooling to room temperature
additionthe mixture was poured into ice
filtrationThe precipitated product was collected by filtration
custompurified by flash column chromatography (eluent DCM:ethyl acetate gradient)

Sources & evidence

ORD record: ord-ef436d2c87974c2f84867c9c3a773282
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158785B2

Reaction notes

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