Sodium Azide → HCID 86662602, compound

HRID 1958064Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[CH3:22])[C:12]2[N:23]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[S:25][C:11]=2[C:10](=[O:32])[N:9]=1)[CH3:7]>CN(C)C=O.O>[N:1]([CH:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[CH3:22])[C:12]2[N:23]=[C:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[S:25][C:11]=2[C:10](=[O:32])[N:9]=1)[CH3:7])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of sodium azide (20.16 mg, 0.310 mmol) in N,N-Dimethylformamide (DMF) (1.5 mL) was added 5-(1-bromoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (100 mg, 0.207 mmol) in N,N-Dimethylformamide (DMF) (1.5 mL). The reaction was heated to 65° C. for 2 hr, and then the solution was cooled to room temperature. The reaction contents were diluted with water, producing a precipitate. The suspension was filtered using a fritted funnel, providing 5-(1-azidoethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (48 mg, 0.108 mmol, 52.1% yield) as a crude brown solid that was used directly in the next reaction. LC/MS m/z MH+=446 (theoretical), found=446.1, 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.67 (d, J=6.82 Hz, 4H) 2.47 (s, 3H) 3.48-3.66 (m, 5H) 3.68-3.87 (m, 5H) 3.97 (q, J=6.57 Hz, 1H) 5.42 (d, J=17.18 Hz, 1H) 5.76 (d, J=17.18 Hz, 1H) 6.41 (d, J=7.58 Hz, 1H) 7.07 (t, J=7.83 Hz, 1H) 7.35 (d, J=8.08 Hz, 1H)

Workup

temperaturethe solution was cooled to room temperature
customThe reaction contents
customproducing a precipitate
filtrationThe suspension was filtered

Sources & evidence

ORD record: ord-be11ad08dd4b4aa98b40ad5262d8472b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410095B2

Reaction notes

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